WO1996019522A1 - Polycarbonate-base polymer, production process, resin coating fluid prepared therefrom, and electrophotographic photoreceptor prepared therefrom - Google Patents

Abstract

A polymer comprising mainly repeating units (1) and/or repeating units (2), containing optionally terminal groups (3) and/or repeating units (4), and having a reduced viscosity [θsp/c] of 0.2 to 10.0 dl/g as measured in a 0.5 g/dl solution thereof in methylene chloride at 20 °C; a resin coating fluid containing the polymer, a charge-transfer substance and a solvent; and an electrophotographic photoreceptor containing the polymer as a binder resin in a photosensitive layer, wherein Rf1 represents a group that is composed of at least carbon and fluorine atoms and bonded directly to the two oxygen atoms of the carbonate linkage in the general formula (1) without any intervening arylene group; and Rf2 represents a group that is composed of at least carbon and fluorine atoms and bonded directly to one of the oxygen atoms of the carbonate linkage in the general formula (3) without any intervening arylene group.

Description

 Description Polycarbonate polymer, manufacturing method, resin coating liquid using the same, and electrophotographic photoreceptor using the same

Technical field

 The present invention relates to a polycarbonate polymer and a resin coating liquid using the same. The present invention further relates to an electrophotographic photoreceptor containing the above-mentioned polycarbonate-based polymer as a binder resin for a photosensitive layer, and more particularly, to an excellent mechanical strength and excellent mechanical strength against repeated use over a long period of time. The present invention relates to an electrophotographic photoreceptor that maintains electrophotographic characteristics and can be suitably used in various electrophotographic fields.

 The present invention also relates to a method for producing a polycarbonate. More specifically, the present invention relates to a polycarbonate capable of stably producing a high-quality aliphatic or aliphatic aromatic polycarbonate having a high molecular weight and having no residual coloring or catalyst used for synthesis. The present invention relates to a method for manufacturing a single component. This method for producing a polycarbonate is suitably used, for example, for synthesizing the polycarbonate-based polymer according to the present invention.

Background art

 In the recent field of electrophotography, a laminated electrophotographic photoreceptor, that is, a photosensitive layer has at least two layers, a charge generation layer (CGL) for generating charges upon exposure and a charge transport layer (CTL) for transporting charges. -Type organic electrophotographic photoreceptors (OPCs) with a single layer and a single-layer type electrophotographic photoreceptor in which the photosensitive layer consists of a single layer in which a charge-generating substance and a charge-transporting substance are dispersed in a binder resin. Have been.

On the other hand, an electrophotographic photoreceptor is required to have predetermined sensitivity, electrical characteristics, and optical characteristics according to an applied electrophotographic process. In particular, for photoreceptors that are used repeatedly, the surface layer of the photoreceptor, that is, the layer located farthest from the substrate (usually a conductive substrate), is provided with corona charging, toner development, transfer to paper, and cleaning. Since electrical and mechanical external forces are directly applied during the process, durability is required. Specifically, friction causes surface wear and scratches, Durability against surface degradation due to ozone generated during all types of corona charging is required. In order to respond to such demands, the binder resin for the charge transport layer of the laminated electrophotographic photosensitive member and the photosensitive layer of the single-layer electrophotographic photosensitive member must be compatible with the charge transport material. Polycarbonate resins made of bisphenol A or bisphenol Z have been widely used because of their good mechanical strength and high mechanical strength. However, the use of polycarbonate resins made from bisphenol A or bisphenol Z is not sufficient to satisfy the above requirements.

 That is, when preparing a coating solution for forming a photosensitive layer by dissolving a polycarbonate resin made of bisphenol A or bisphenol Z as a raw material, the coating solution is whitened or gelled, and The photographic layer after processing and drying may be crystallized. In the portion where the crystallization occurs, there is no light decay, and the charge remains as a residual potential, and appears as a dif- ference in image quality.

 In addition, a photoreceptor using a polycarbonate resin made of bisphenol A or bisphenol Z suffers from abrasion and scratches due to insufficient surface hardness, resulting in poor durability.

By the way, bisphenol A polycarbonate obtained by reacting 2,2-bis (4-hydroxyphenyl) propane (bisphenol A) with a carbonate precursor such as phosgene diphenyl carbonate is a typical and conventionally known representative. Polycarbonate is widely used as an engineering plastic because of its excellent properties such as transparency, heat resistance, and mechanical properties. However, in recent years, with the expansion of uses of polycarbonate, the development of polycarbonate having more excellent physical properties has been desired, and polycarbonates having various structures have been proposed. In addition, with the expansion of applications, there is a growing demand for the development of polycarbonates having various functions in accordance with the application and having even higher performance in addition to the above-mentioned physical properties. Examples of polycarbonates that meet such demands include the use of alcohol compounds as reaction raw materials, aliphatic polycarbonates, aliphatic aromatic polycarbonates, and specialty polycarbonates. Polycarbonate having a high aliphatic terminal group. However, since alcohol compounds have low reactivity, they do not react in the interfacial polycondensation method, which is a general method for producing polycarbonates, but in aliphatic polycarbonates obtained by the interfacial polycondensation method. Synthesis of aliphatic and aromatic aromatic polycarbonates and introduction of aliphatic terminal groups have been considered impossible. Therefore, in the synthesis of polycarbonate using such an alcohol compound, a melt polymerization method which is a polymerization method of polycarbonate other than the interfacial polycondensation method has been conventionally used. However, in the melt polymerization method, there is a disadvantage that the catalyst in the reaction system remains in the polymer.In addition, since the reaction in the melt polymerization method is performed at a high temperature, the polymer is discolored, etc. No characteristic polymer was obtained. Disclosure of the invention

 The present invention has been made in view of the above circumstances, and has been made to solve the above-described problems observed in an electrophotographic photoreceptor using polycarbonate made of bisphenol A or bisphenol Z as a binder resin. With the goal. That is, an object of the present invention is to provide a polymer which has good compatibility with a charge transport material, does not cause whitening or gelation even when dissolved in a solvent, and has high surface hardness and abrasion resistance. To do so. The present invention also provides a coating solution obtained by dissolving the polymer and the charge transporting substance in a solvent, which does not cause whitening or gelation over a long storage period and exhibits excellent stability. An object of the present invention is to provide a resin coating liquid suitably used for forming the charge transport layer. Still another object of the present invention is to provide an electrophotographic photoreceptor using the above polymer as a binder resin, the electrophotographic photoreceptor maintaining excellent abrasion resistance and electrophotographic characteristics over a long period of time. And

 Further, the present invention solves the problems of the method for producing polycarbonate found in the prior art described above, and uses an alcohol compound as a raw material, has a high molecular weight, and has no catalyst remaining or coloring. It is an object of the present invention to provide a production method capable of easily and stably producing by the interfacial polycondensation method.

The present inventors have conducted intensive studies to solve the above problems, and as a result, a structural unit consisting of at least a carbon atom and a fluorine atom and directly bonded to an oxygen atom of a carbonate bond without passing through an arylene group When using a polycarbonate-based polymer as a binder resin, the coating solution does not whiten or gel during photoconductor production, and has excellent electrophotographic properties and durability over a long period of use. It has been found that an electrophotographic photoreceptor that maintains the properties can be obtained. Was completed.

 [Polymer]

That is, the present invention provides a reduced viscosity at 20 ° C. of a solution having a concentration of 0.5 g / d 1 using a repeating unit (1) represented by the following general formula (1) as a main component and methylene chloride as a solvent. [7? _SP no c] is 0.2 to 10.0 d1 / _g , and a polymer (polymer A) is provided. One 0— Rf ¹ — 0— C one (1)

 II

0 (In the formula, R f ¹ is a group composed of at least a carbon atom and a fluorine atom and directly bonded to each oxygen atom of the carbonate bond in the general formula (1) without passing through an arylene group. Represents.)

Further, the present invention comprises a repeating unit (2) represented by the following general formula (2) as a main component, and a part or all of the polymer terminal is a terminal group (3) represented by the following general formula (3) The reduced viscosity [7? _SP / c] at 20 ° C of a solution of 0.5 gZd I in methylene chloride as a solvent should be 0.2 to 10 · 0 · d1 / g. The present invention provides a polymer characterized by the following (polymer D).

(In the general formula (2), R ⁵ and R ⁵¹ are each independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, substitution of 6 to 12 carbon atoms or represents unsubstituted Ariru group, W is a single bond, - 0-, one CO-, - S-, - SO - , - S0 2 -, - CR 52 R 53 - (R 52 and R ⁵³ are each independently A hydrogen atom, a trifluoromethyl group, an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.), A cycloalkylidene group having 5 to 11 carbon atoms or carbon number 2 to 12, ω-alkylene group, 9-fluorenylidene group, 1,9-menthenyl group, substituted or unsubstituted pyradylidene group, substituted or unsubstituted carbon Represents an arylene group of the formulas 6 to 12 or an α, ω-siloxanediyl group, and Α and Β each independently represent an integer of 0 to 4. )

-O- C-0-Rf ^ (3)

 II

 0

(In the general formula (3), R f ² is composed of at least a carbon atom and a fluorine atom, and is directly bonded to an oxygen atom of a carbonate bond in the general formula (3) without passing through an arylene group. Represents a group.)

 [Resin coating liquid]

 Further, the present invention provides a resin coating solution comprising the above-mentioned polymer of the present invention, a charge transport substance and a solvent.

 [Electrophotographic photoreceptor]

 The present invention further provides an electrophotographic photoreceptor having a photosensitive layer containing a charge generating substance, a charge transporting substance and a binder resin on a conductive substrate, wherein the photosensitive layer is a binder resin, It is intended to provide an electrophotographic photoreceptor characterized by using coalescence.

 [Polycarbonate production method]

Further, the present inventor has ports Rica by interfacial polycondensation using an aliphatic alcohol as a raw material - Bone Bok method of synthesizing a result of extensive studies of the raw material alcohol an alcohol having a p K _a smaller PK _a water It has been found that the use as a compound makes it possible to synthesize aliphatic polycarbonate, aliphatic aromatic polycarbonate, and aliphatic group-terminated polycarbonate by the interfacial polycondensation method. The present invention has been completed. For example, the production method of the present invention can be suitably used for synthesizing the polymer of the present invention.

Here, the p K _a, Ru value der wearing a negative sign logarithm of the acidity constant (K a).

PKa =-lOgKa Equation (1) The acidity constant Ka is defined as follows. If a general acid is HA, then in water. HA + H ₂ 0 = H ₃ 0 '+ A— equilibrium state of equation (2),

The equilibrium constant K _eq is

[Η ₃ 0 '] [A-]

 Ke equation (3)

[HA] becomes [H ₂ 0]. ([] Indicates the concentration of each chemical species.)

In a normal dilute solution, the water concentration [H ₂ 0] hardly changes and remains constant at 55.5 M. Therefore, the equilibrium constant K _eq can be expressed as another equation as follows. This constant is the acidity constant K _a.

[A—] [H ₃ 0

K _a = Equation (4)

[HA] In the synthesis reaction of polycarbonate Bok by interfacial polycondensation, for alcohol compound to produce a reactive species, acid-binding agent with the acid-binding agent in the _c interfacial polycondensation it is necessary to react the because it uses dissolved in water, larger than PK _a of water

Alcohol compounds having P do not react with the acid binder. That is, since the pK _a of the water is 1 5. 74 large alcohol compound from the p K _a is 1 5. 74, can not form a chemical species necessary for the polycondensation reaction with the acid-binding agent, polymerization The reaction cannot be performed.

Therefore, in the present invention, in synthesizing a polycarbonate using an alcohol compound as at least a part of a raw material, an alcohol compound having _a pKa of less than 15.74 is used. The synthesis of polycarbonate is possible.

That is, the present invention further provides a polycarboxylate that is subjected to interfacial polycondensation in a mixture of an organic solvent insoluble in water and an aqueous solution of an alkali using a carbonate-forming compound and a dioxy compound in the presence of an aqueous alkaline solution. In the method for producing There is provided a polycarbonate one Bone Bok manufacturing method which comprises using a p K _a is 1 5.74 less than bivalent alcohol Ichiru in water at 25 ° C as objects.

BRIEF DESCRIPTION OF THE FIGURES

FIG. 1 is a ¹ H-NMR chart of the polymer produced in Example 1.

 FIG. 2 is an 'H—N MR chart of the polymer produced in Example 4.

FIG. 3 is a ¹ H-NMR chart of the polymer produced in Example 7.

 FIG. 4 is an 'H-NMR chart of the polymer produced in Example 10.

 FIG. 5 is an 'H-NMR chart of the polymer produced in Example 13.

 FIG. 6 is an 'H-NMR chart of the polymer produced in Example 16.

 FIG. 7 is an 'H-NMR chart of the polymer produced in Example 19.

FIG. 8 is a ¹ H-NMR chart of the polymer produced in Example 20.

 FIG. 9 is an 'H-NMR chart of the polymer produced in Example 21.

FIG. 10 is a ¹ H-NMR chart of the polymer produced in Example 22.

FIG. 11 is a ¹ H-NMR chart of the polymer produced in Example 23.

BEST MODE FOR CARRYING OUT THE INVENTION

 [1] polymer

 As the polycarbonate-based polymer of the present invention, for example, polycarbonate, polyester carbonate, and the like are preferred; and poly-polycarbonate is particularly preferred.

The polymer A provided by the present invention is a polycarbonate-based polymer having the following repeating unit (1>) as a main component. 1—Rf ¹ —0—C— (1)

 II

 0

(In the formula, R f ¹ has the same meaning as described above.)

The polymer A may have two or more kinds of repeating units (1), and may have other repeating units (other than 1) as long as the object of the present invention is not hindered. It may be. The polymer A may be linear, cyclic, or branched. Furthermore, by using a terminal terminator or a branching agent during the synthesis of the polymer, the obtained polymer may have a special terminal structure introduced at the terminal or a special branch structure introduced. Is also good.

 R f ′ in the repeating unit (1) is composed of at least a carbon atom and a fluorine atom. In addition to the carbon atom and the fluorine atom, a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a gay element atom, a phosphorus atom, It may contain a boron atom, a chlorine atom, a bromine atom, an iodine atom and the like. In particular, it preferably contains a hydrogen atom.

Examples of those having a preferable structure as R f ¹ include, for example, a fluorine-substituted alkylidene group, a fluorine-substituted alkylene group, a fluorine-substituted cycloalkylidene group, and a fluorine-substituted cycloalkylene group. Further, the above-mentioned fluorine-substituted alkylidene group and fluorine-substituted alkylene group may have a straight-chain structure or a branched structure. Unless it is located at the terminal of each group, the structure may have an arylene group such as a phenylene group.

 Particularly preferred examples of R f ′ include those having the following structures.

CH ₂ — (CF ₂ ) _r -CH ₂ —, -CH-, one CH—CH ₂ — -CH- CH ₂ —

(CF ₂ ) _r F (CF ₂ ) _r F CH ₂ (CF ₂ ) _r F

(CF ₂ ) _r F (CF ₂ ) _r F CH ₂ (CF ₂ ) _r F (CF ₂ ) _r F -C- -CH-CH- CH-CH-, one C-one CH _2- (CF ₂ ) _S F (CF ₂ ) _S F CH ₂ (CF ₂ ) _S F (CF ₂ ) _S F

CH ₂ (CF ₂ ) _r F (CF ₂ ) _U F (CF ₂ ) _r F

-C-CH _2-

CH ₂ (CF ₂ ) _S F (CF ₂ ) vF (CF ₂ ) _S F (CF ₂ ) vF (CF ₂ ) _S F

(In the formula, r, s, u and v each independently represent an integer of 1 to 20, preferably 1 to 10.)

The polymer A of the present invention is prepared by dissolving 0.5 _g / d 1 in methylene chloride as a solvent. The reduced viscosity of the liquid at 20 ° C. is 0.2 to 10.0 d 1 g. If the reduced viscosity is less than 0.2 dl Zg, it tends to wear due to insufficient hardness, and the printing life is shortened. If the reduced viscosity exceeds 10.0 d 1 g, the solution viscosity of the polymer And the production of the polymer itself becomes difficult, or the production of the photoreceptor by applying a coating liquid may become difficult. More preferably, it is 0.3 to 2. O dl Zg.

Further, the present invention provides a polymer having a repeating unit other than the repeating unit (1) represented by the general formula (1) among the above polymer A, which is preferably a repeating unit (1) or a compound represented by the following general formula: The repeating unit (2) represented by (2) is the main component, and the ratio of the repeating unit (1) to the total of the repeating unit (1) and the repeating unit (2) is 0.1 to 99 mol%. And a reduced viscosity [7? _Sp Zc] at 20 ° C of a solution having a concentration of 0.5 gZ d 1 using methylene chloride as a solvent is 0.2 to 10 O dl Z g, preferably 0.3 to The present invention provides a polymer (Polymer B) characterized by being 2.0 d 1.

(In the general formula (2), R 5 and R ⁵ ′ are each independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, or a substitution having 6 to 12 carbon atoms. or represents unsubstituted Ariru group, W is a single bond, -0-, - CO-, - S- , - SO -, - S 0 2 -, - CR 52 R 53 - (R 52 and R ⁵³ are each Independently a hydrogen atom, a trifluormethyl group, an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.), Cycloalkylidene having 5 to 11 carbon atoms 12 or α, ω-alkylene group, 9-fluorenylidene group, 1,9-nonylbenzyl group, substituted or unsubstituted pyradylidene group, substituted or unsubstituted carbon number 6 to 1 2 represents an arylene group or an α, ω-siloxanediyl group, and Α and Β each independently represent an integer of 0 to 4.)

Examples of the halogen atom which is an example of R ⁵ ° and R ^{51 in} the general formula (2) include a fluorine atom , Chlorine, bromine and iodine atoms. Particularly, a chlorine atom and a bromine atom are preferable.

Preferred specific examples of the alkyl group having 1 to 6 carbon atoms which are examples of R ⁵ ° and R ⁵¹ include, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, and isopropyl group. , Isobutyl group, sec-butyl group and tert-butyl group. Particularly, a methyl group is preferred.

R ^5. And preferably a cycloalkyl group having a carbon number of 5-7 is an example of R ^51! ^, Is a specific example, for example, a cyclopentyl group, a cyclohexyl group, heptyl group there Ru cyclohexylene. Particularly, a cyclohexyl group is preferred.

Preferred specific examples of the substituted or unsubstituted aryl group having 6 to 12 carbon atoms as examples of R ⁵ ° and R ⁵¹ include, for example, a phenyl group, a tryl group, a xylyl group, a naphthyl group and a benzyl group. is there. Particularly, a phenyl group is preferable.

R ⁵ ° and R ⁵¹ may be the same or different. Are examples of W in the general formula (2) - in CR ^{5 2} R 53 primary, as preferred correct specific examples of the alkyl group of R ⁵² and the carbon number of 1-1 0 is an example of R ⁵³ is, for example, main Tyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, isobutyl, sec-butyl, tert-butyl, etc. . Particularly, a methyl group, an ethyl group, a propyl group, and an isopropyl group are preferred.

Preferred specific examples of the substituted or unsubstituted aryl group having 6 to 12 carbon atoms as examples of R ⁵² and R ⁵³ include, for example, phenyl, tolyl, xylyl, naphthyl and benzyl . Particularly, a phenyl group is preferable.

Preferred ingredients body examples of consequent opening alkylidene group having a carbon number of 5-1 1 is an example of R ⁵² and R ⁵³ are, for example, cyclopentylidene group, cyclohexylidene group to cycloalkyl, cycloalkyl heptylidene group, a cycloalkyl O Chi isopropylidene group, 3 , 3,5- There is a trimethylcyclohexylidene group. Particularly, a cyclohexylidene group is preferred.

Preferred examples of the α, ω-alkylene group having 2 to 12 carbon atoms as examples of R ⁵² and R ⁵³ include, for example, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, Heptamethylene group, Octamethylene group, Nona There are methylene group and decamethylene group. Particularly, an ethylene group is preferable.

Preferred examples of embodiment a which Ariren group with carbon number 6-1 2 R ⁵² and R ⁵³ are phenylene group, there is Jifue two alkylene groups.

Note that R ⁵² and may be the same or different. In the case of the polymer B having the repeating unit (1) and the repeating unit (2), the repeating unit (1) is 0.1 to 99 as a percentage of the total of the repeating unit (1) and the repeating unit (2). Mol%, preferably 1 to 50 mol%. If the proportion of the repeating unit (1) is less than 0.1 mol%, the effects of the present invention cannot be obtained, and whitening and gelation of the coating solution and crystallization of the charge transport layer and the photosensitive layer are prevented. In addition, it is impossible to improve the printing life. On the other hand, if the proportion of the repeating unit (1) exceeds 99 mol%, the solubility in the solvent and the stability of the solution during the preparation of the coating liquid may be reduced or the crystallization may occur depending on the type of the repeating unit (1). Whitening may occur. The polymer B may also have two or more kinds of the repeating unit (1) and the repeating unit (2), respectively. It may have a unit.

Furthermore, the present invention provides a polymer having a preferred terminal structure among the above-mentioned polymer A having a repeating unit (1) as a main component, wherein the polymer A has a repeating unit (1) as a main component and a part or all of the polymer terminal. Is terminated by a terminal group 3) represented by the following general formula (3), and the reduced viscosity at 20 ° C of a 0.5 gZd 1 solution using methylene chloride as a solvent [7 / _sp / c] Is 0.2 to 10.0 d 1 / g, preferably 0.3 to 2.0 d 1 Zg.

-OC-0-Rf ² (3)

 II

 0

(In the general formula (3), R f ² represents a group composed of at least a carbon atom and a fluorine atom and directly bonded to an oxygen atom of a carbonate bond in the general formula (3) without passing through an arylene group. )

R f ² in the terminal group (3) is composed of at least a carbon atom and a fluorine atom. In addition to the carbon atom and the fluorine atom, a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a gay atom, a phosphorus atom, and a boron atom Atom, chlorine atom, bromine atom, iodine atom etc. Good. In particular, it preferably contains a hydrogen atom.

Examples of those having a preferable structure as R f ² include a fluorine-substituted alkyl group and a fluorine-substituted cycloalkyl group. Further, the fluorine-substituted alkyl group may have a straight-chain structure or a branched structure.

Particularly preferred examples of R f ² include those having the following structures.

F- (CF ₂ ) _r -CH _2- , F- (CF ₂ ) _r -CHFCF ₂ CH _2- , F— (CF ₂ ) _r — (C) _s- ,

F- (CF ₂ ) _r O-CF-CH _2- , F- (CF ₂ ) _r -CF-CH _2- , H— (CF ₂ ) _r — CH ₂ —,

CF ₃ CF ₃

F- (CF ₂ ) _S H— (CH ₂ ) _S H- (CH ₂ ) _s 0

F- (CF ₂ ) _r ~ CH-, F- (CF ₂ ) _r -CH-, F— (CF ₂ ) _r — CH-

(In the formula, r and s each independently represent an integer of 1 to 20, preferably 1 to 10.) The polymer C also has two or more types of the repeating unit (1) and the terminal group (3). May be.

Further, the present invention comprises a repeating unit (2) represented by the general formula (2) as a main component, and a part or all of the polymer terminal is a terminal group (3) represented by the general formula (3). The reduced viscosity at 20 ° C [7? _SP / c] of a solution with a concentration of 0.5 gZd1 using methylene chloride as a solvent should be 0.2 to 10.0 d1 / g. The present invention provides a polymer characterized by the following (polymer D).

 This polymer D has a reduced viscosity at 20 ° C. of a solution having a concentration of 0.5 gZd 1 in methylene chloride as a solvent of 0.2 to 10.0 d 1 / g. If the reduced viscosity is less than 0.2 d 1 / g, it is liable to wear due to insufficient hardness, and the printing life is shortened. If the reduced viscosity exceeds 10.0 d 1 / g, the polymer becomes In some cases, the solution viscosity may increase, and the production of the polymer itself may become difficult, or the production of the photoreceptor by applying a coating liquid may become difficult. More preferably, it is 0.3 to 2. OdlZg.

This polymer D also has two or more types of repeating unit (2) and terminal group (3). It may have a repeating unit or terminal group other than those described above within a range that does not hinder the achievement of the object of the present invention.

 The polymer D may be linear, cyclic, or branched.In addition, a special branching structure is introduced into the obtained polymer by using a branching agent or the like during the synthesis of the polymer. May be used.

 In the polymer D mainly composed of the repeating unit (2), the ratio of the terminal group (3) to the total of the repeating unit (2) and the terminal group (3) is 0.01 to 30 mol%, Preferably, the ratio is 1 to 10 mol%. If the proportion of the terminal group (3) is less than 0.01 mol%, the effects of the present invention cannot be obtained, and whitening and gelation of the coating solution, prevention of crystallization of the charge transport layer and the photosensitive layer, and the like can be prevented. It may be impossible to achieve an increase in the printing life.

Further, the present invention provides a polymer B having the repeating unit (1) and the repeating unit (2) as a main component, which has a preferable terminal structure, and is characterized by a total of the repeating unit (1) and the repeating unit (2). The ratio of the repeating unit (1) to the polymer is 0.1 to 99 mol%, and a part or all of the polymer terminal is terminated by the terminal group (3) represented by the general formula (3); A solution having a concentration of 0.5 g / d 1 in methylene chloride as a solvent has a reduced viscosity [“ _sp / c] at 20 ° C. of 0.2 to 10 OdlZg, preferably 0.3 to 2. It provides a polymer that is 0 d 1 Zg (Polymer E).

 Further, the present invention provides, among the above various polymers A to E of the present invention, those having a preferable branched structure.

That is, the present invention has a repeating unit (1) as a main component, and further has a repeating unit (4) represented by the following general formula (4) as a branch unit. The repeating unit (4) and the repeating unit (4) The ratio of the repeating unit (4) with respect to the total of the repeating units other than the above is 0.01 to 30 mol%, and the reduction at 20 ° C of a solution having a concentration of 0.5 g / d 1 in methylene chloride as a solvent is performed. Provide a polymer (Polymer F) having a viscosity [7? _SP Zc] of 0.2 to 10.0 d 1 / g. R54

(In the general formula (4), R ⁵⁴ represents an alkyl group having 1 to 10 carbon atoms.)

R ⁵⁴ in the general formula (4) is an alkyl group having 1 to 10 carbon atoms. Specific preferred examples thereof include a methyl group, an ethyl group, a propyl group, and a butyl group, and a methyl group is particularly preferred.

Further, the present invention has the repeating unit (1) and the repeating unit (2) as main components, and further has the above-mentioned repeating unit (4) as a branching unit, and comprises the repeating unit (1) and the repeating unit (2). The ratio of the repeating unit (1) to the total is 0.1 to 99 mol%, and the ratio of the repeating unit (4) to the total of the repeating unit (4) and the repeating unit other than the repeating unit (4) Is 0.11 to 30 mol%, and the reduced viscosity [ _{S l} , / c] of the solution of 0.5 gZd1 in methylene chloride as a solvent at 20 ° C. is 0.2 to 10 mol%. 0 d 1 / g. (Polymer G)

 Further, the present invention has a repeating unit (1) as a main component and further has the above-mentioned repeating unit (4) as a branching unit, and a repeating unit based on the total of the repeating unit (4) and the repeating unit other than the repeating unit (4) The ratio of (4) is 0.01 to 30 mol%, a part or all of the polymer terminal is terminated by a terminal group (3), and the concentration of the solvent in methylene chloride is 0.5 g. The present invention provides a polymer (Polymer H) having a reduced viscosity [7 / spZc] at 20 ° C of the solution of / d1 of 0.2 to 10.0 d1 / g.

Furthermore, the present invention has a repeating unit (2) as a main component, and further has the above-mentioned repeating unit (4) as a branching unit, and is a repeating unit based on the total of the repeating unit (4) and the repeating unit other than the repeating unit (4). The ratio of (4) is 0.01 to 30 mol%, a part or all of the polymer terminal is terminated by a terminal group (3), and a concentration of 0.5 gZd using methylene chloride as a solvent. providing reduced viscosity at 2 0 C the first solution [7? _SP Z c] is 0.2 to 1 0. a 0 d 1 polymer (polymer]). Further, the present invention has a repeating unit (1) and a repeating unit (2) as main components, and further has the repeating unit (4) as a branching unit, wherein the repeating unit (1) and the repeating unit (2) The ratio of the repeating unit (1) to the total is 0.1 to 99 mol%, and the ratio of the repeating unit (4) to the total of the repeating unit (4) and the repeating units other than the repeating unit (4) is 0. 01 to 30 mol%, part or all of the polymer ends are terminated with terminal groups (3), and reduction of a 0.5 d1 solution using methylene chloride as a solvent at 20 ° C Provide a polymer (Polymer J) having a viscosity [7? _SP Zc] of 0.2 to 10.0 d 1.

 [2] Production of polymer

 The polymer A of the present invention containing the above-mentioned repeating unit (1) as a main component can be obtained by appropriately combining a dihydric alcohol (I) represented by the following general formula (I) with a carbonate-forming compound such as phosgene. It can be produced by polycondensation in the presence of an acid binder or by a method such as transesterification between dihydric alcohol (I) and bisaryl carbonate.

HO—Rf ¹ —OH (I) (wherein, R f ′ has the same meaning as described above.)

As the dihydric alcohol (I), a dihydric alcohol having a structure having at least one fluorine atom at the carbon (^ position) adjacent to the carbon to which each hydroxyl group is bonded or at the carbon (7 position) adjacent thereto Is preferred. Preferred examples of the dihydric alcohol (I) include those represented by the following structural formula. _{HO- CH 2 - (CF 2)} r one CH ₂ one OH, HO- CH- OH, HO- CH- CH 2 primary OH, HO- CH- CH ₂ primary OH

(CF ₂ ) _r F (CF ₂ ) _r F CH ₂ (CF ₂ ) _r F

(CF ₂ ) _r F (CF ₂ ) _r F CH ₂ (CF ₂ ) _r F (CF ₂ ) _r F

HO-C-OH, HO - CH - CH- OH, HO - CH - CH - OH, HO-C-CH 2 -OH (CF 2) S F (CF 2) S F CH 2 (CF 2) S F (CF ₂ ) _S F

CH ₂ (CF ₂ ) _r F (CF ₂ ) _U F (CF ₂ ) _r F (

(CF₂)vF (CF₂)_SF HO-C— CH ₂ — 0H, HO- CH ₂ (CF ₂ ) _S F

(CF ₂ ) vF (CF ₂ ) _S F

(In the formula, r, s, u and v have the same meaning as described above.)

Specific examples of the above dihydric alcohol (I) include 2,2-difluoro-1,3-propanediol, 2,2,3,3-tetrafluoro-1,4-butanediol, 2,2,3 3,4,4-Hexafluoro-1,5-pentanedole, 1 H, 1 H, 6 H, 6 H—Perfluoro-1,6-hexanediol, 1 H, 1 H, 7 H, 7 H— Perfluoro-1,7-heptanediol, 1H, 1H, 8H, 8H-Perfluoro-1,8-octanediol, 1H, 1H, 9H.9H-Perfluoro-1,9-nonanediol, 1H , 1 H, 10 H, 10 H—Perfluoro-1,10-decanediol, 1 H, 1 H, 11 H, 11 H—Perfluoro-1,1,1-decanediol, 1 H, 1 H, 12 H, 12 H—perfluoro; , 1 2—dodecanediol, 2,2,2_trifluoro 1,1,1-ethanediol, 2,2,3,3,3-pentafluoro-1,1-ethanediol, 1H-perfluoro-1,1- Butanediol, 1 H—perfluoro 1,1 pentanediol, 1 H—perfluoro 1,1,1 hexanediol, 1 H—perfluoro 1,1,1-heptanediol, 1 H—perfluoro 1,1,1 Octanediol, 1H-perfluoro-1,1-nonanediol, 1H-perfluoro-1,1-decanediol, 1H-perfluoro-1,1,1-decanediol, 1H-perfluoro-1,1-dodecanediol, 3,3,3-trifluoro-1,2-propanediol, 1H, 1H, 2H-puff Luolow 1,2-butanediol, 1H, 1H, 2H-perfluoro-1,2-pentanediol, 1H, 1H, 2H-perfluoro-1,2-hexanediol, 1H, 1H, 2H —Perfluoro-1,2—heptanediol, 1 H, 1 H, 2H—Perfluoro-1,2-octanediol, 1 H, 1 H, 2 H-Perfluoro-1,2-nonanediol, 1 H, 1 H 1,2-decanediol, 1H, 1H, 2H-perfluoro-1,2, -pentanediol, 1H, 1H, 2H-perfluoro-1,2, -dodecanediol, 1H , 1H, 2H-perfluoro-1,2-tridecanediol, 1H, 1H, 2H-perfluoro-1,2-tetradecanediol, 4,4,4-trifluoro-1,2-butanediol, 4,4,5,5,5-pentafluoro-1,2-pentanediol, 1H, 1H, 2H, 3H, 3H-perfluoro 1,2-Hexanediol, 1H, 1H, 2H, 3H, 3H-Perfluoro-1,2heptanediol, 1H, 1H, 2H, 3H, 3H-Perfluoro-1,2-octanediol, 1 H, 1 H, 2 H, 3 H, 3 H—perfluoro 1,2 nonanediol, 1 H, 1 H, 2 H, 3 H, 3 H—perfluoro 1,2—decane, 1 H, 1 H, 2 H, 3H, 3 H—perfluoro-1,2-dendanediol, 1 H, 1 H, 2H, 3 H, 3H—perfluoro-1,2-dodecanediol, 1 H, 1 H, 2 H, 3 H , 3H—Perfluoro-1,2—tridecanediol, 1H, 1H, 2H, 3H, 3H Perfluoro-1,2—tetradecanethiol, 1H, 1H, 2H, 3H, 3H—Perfluoro1.2.2—Penfluorodecanediol, 1H, 1H, 2H, 3H, 3H—Perfluoro—1,2_hexadenediol, Perfluoropropane-1 2-diol, perfluorobutane 2, 2-di Perfluoropentane-1,3-diol, perfluorodecane 2,2-diol, perfluorododecane 2,2-diol, verfluorate tradecan-1,2,2-diol, 2H, 3H-perdiol Fluorobutane-1,2,3-diol, 2H, 3H-Perfluoropentane-1,2,3-diol, 2H, 3H-Perfluorooundecan-1,2,3-diol, 2H, 3H-Perfluorotridecane-1 2,3-diol, 2H, 3H perfluoropentadecane 2,3-diol, 2H, 2H, 3H, 4H, 5H, 5H 3,4-diol, 2H, 2H, 3H, 4H, 5H, 5H—perfluoroheptan-3,4-diol, 2H, 2H, 3H, 4H, 5H, 5H— Perfluorotridecane-1,3-diol, 2-perfluoromethyl-1H, 1H-perfluoropropane-1,2-diol, 2-perfluoromethyl-1H, 1H-perfluorodecane-1, 2-diol, 2-perfluoromethyl-1H, 1H-perfluorododecane-1,2-diol, 2- (1H, 1H-perfluoroethyl) 1-1H, 1H, 3H, 3 H—Perfluorobutane—1, 2-diol, 21 (1 H, 1 H—Perfluoroethyl) 1 1 H, 1 H, 3 H, 3 H—Perfluorooundecan—1,2—diol , 2— (1H, 1H—perfluoroethyl) —1H, 1H, 3H, 3H—perfluorotridecane-1,1,2-diol, 1,4—bis (2-hydroxyperf Luollow 2—Pro Le) benzene, 1, 3- bis (2-arsenide Dorokishipa one Furuoro 2-propyl) benzene, 1, 4 one-bis (2-hydroxycarboxylic perfluoro-2-decyl) benzene.

The polymer B of the present invention comprising the above-mentioned repeating unit (1) and the repeating unit (2) as main components includes the above-mentioned dihydric alcohol (I) and a dihydroxylaryl compound (II) represented by the following general formula (II). ) And a carbonate-forming compound such as phosgene in the presence of a suitable acid binder, or alternatively, an ester of dihydric alcohol U) or dihydroxyaryl compound (II) with bisarylcarbonate. It can be produced by a method such as an exchange reaction.

(Wherein, R ⁵ , R ^5I , W, A and B have the same meanings as described above.)

Specific examples of the above-mentioned dihydroxyl compound (II) (dihydroxyl compound group (II-a)) include 4,4'-dihydroxybiphenyl, 3,3'-difluoro4,4 '—Dihydroxybiphenyl, 4, 4'—Dihydroxy3,3'-Dimethylbiphenyl, 4, 4 '—Dihydroxy-1,2,2'-Dimethylbiphenyl, 4,4' Dihydrobiphenyl 4,4 'dihydroxybiphenyls such as 3,3'dicyclohexylbiphenyl; bis (4-hydroxyphenyl) Methane, 1,1-bis (4-hydroxyphenyl) 1-1,1-diphenylmethane, 1,1-bis (4-hydroxyphenyl) 1-1-phenylmethyl.bis (4-hydroxyphenyl) 3-methylphenyl) methane, bis (3-nonyl 4-hydroxy xyphenyl) methane, bis (4-hydroxy-1,3,5-dimethylphenyl) methane, 1,1-bis (2-tert-butyl) 1-4-Hydroxy-5-methylphenyl 1-1-methanemethane, bis (3-chloro-1-phenyl-4-methane), bis (3-fluoro-4-hydroxyphenyl) methane, bis (3,5-dibromo-1) 4-Hydroxyphenyl) methane, Bis (3-arylu 4-Hydroxyphenyl) methane, Bis (2-Hydroxyphenyl) methane, 2-Hydroxyphenyl 4-Hydroxyphenyl Chlorobenzene, bis (2-hydroxy-4-methylphenyl) methane, bis (6-tert-butyl-12-hydroxy-14-methylphenyl) methane, bis (2-hydroxy-14,6-dimethylphenyl) Enyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, 1,2-bis (4-hydroxyphenyl) ethane, 1,1-bis (4-hydroxyphenyl) 1-1,1-phenylethane , 1,1-bis (4-hydroxy-1-methylphenyl) 1-1-phenylethane, 1,1-bis (4-hydroxy-3- phenylphenyl) 1-1-phenyl, 2- (4-hydroxyphenyl) 1-Methylphenyl) 2- (4-Hydroxoxyphenyl) 1-1-Phenylethane, 1,1-bis (2-tert-butyl-14-hydroxy-3-methylphenyl) ethane, 1-Phenyl 1,1-bis (3-fluoro-4-hydroxyphenyl) ethane, 1,1-bis (2-hydroxy-4-methylphenyl) ethane, 2,2-bis (4-hydroquinphenyl) propane (alias) : Bisphenol A), 1,1-bis (4-hydroxyphenyl) propane, 2,2-bis (4-hydroxy-13-methylphenyl) prono ", 2,2-bis (4-hydroxy3, 5 _ (dimethylphenyl) propane, 2,2-bis (3-isopropyl-14-hydroxyphenyl) propane, 2,2-bis (4-hydroxy-12-methylphenyl) propane, 1,1-bis (2-tert-butyl) Butyl 4-hydroxy-5-methylpropane, 2,2-bis (3-sec-butyl-4-hydroxyphenyl) propane, 2,2-bis (3-chloro-4-hydroxy) Yl) propane, 2, 2- bis (3-Furuo Mouth_4—Hydroxyphenyl) propane, 2,2-bis (3-bromo-4-hydroxyphenyl) propane, 2,2-bis (3,5-difluoro-4-hydroxyphenyl) propane (alias: Tetraflu) Orobibisphenol A, 2,2-bis (3,5-dichloro-4-hydroxyphenyl) propane (alias: Tetraclo-mouth bisphenol A), 2,2-bis (3,5-Jib mouth 4-) (Hydroxyphenyl) propane (alias: tetrabromobisphenol A;), 2,2-bis (3-promo 5-chloro-1,4-hydroxyphenyl) propane, 2,2-bis (3-hydroxyphenyl) -1 , 1,1,3,3,3-hexafluoropropane, 2,2-bis (4-hydroxy-13-phenylphenyl) propane, 2,2-bis (3-aryl-1-hydroxyphenyl) ) Propane, 2,2-bis (2-hydroxy 4,6-dimethylphenyl) propane, 2,2-bis (4-sec-butyl-2-hydroxyphenyl) propane, 1,1-bis (2- tert-butyl 5-methyl-4-hydroxyphenyl-1,2-methylpropane, 1,1-bis (4-hydroxyphenyl) -12-methylpropane, 2,2-bis (4-hydroxy-3-) Methylphenyl) butane, 2,2-bis (4-hydroxyphenyl) butane, 1,1-bis (2-butyl-4-hydroxy-15-methylphenyl) butane, 1,1-bis ( 2 _tert-butyl-1-4-hydroxy-5-methylphenylbutane, 1,1-bis (4-hydroxy-2-methyl-5tert-pentylphenyl) butane, 2,2-bis (3,2-bis) 5—Dichro mouth—41 Hydroxifue Le) Butane, 2,2-bis (3,5-dibutene 4-butoxyphenyl) butane, 2,2_bis (4-hydroxyphenyl) 1-3-methylbutane, 1,1-bis (4- (Hydroxyphenyl) 1,3-methylbutane, 2,2-bis (4-hydroxyphenyl) pentane, 1,1,1-bis (4-hydroxyphenyl) cyclopentane, 2,2-bis (4-hydroxyphenyl) hexane, 2-Ethyl-1,1-bis (4-hydroxypropyl) hexane, 4,4-bis (4-hydroxyphenyl) heptane, 1,1-bis (2-tert-butyl-4-hydroxy-5-methylphenyl) heptane 1,2-bis (4-hydroxyphenyl) octane, 2,2-bis (4-hydroxyphenyl) nonane, 2,2_bis (4-hydroxyphenyl) decane, 1,1-bis (4 -Hydroxyv Phenyl) cyclohexane, 1,1-bis (4-hydroxy-13-methylphenyl) cyclohexane, 1,1 bis (4-hydroxy-3,5-dimethylphenyl) cyclohexane, 1 Bis (hydroquinphenyl) alkanes such as 1,1-bis (4-hydroxy-3-cyclohexylphenyl) cyclohexane, 1,1-bis (4-hydroxy-3-phenylphenyl) cyclohexane; bis Bis (4-hydroxyphenyl) ethers such as (4—hydroxyphenyl) ether and bis (3-fluoro-4—hydroxyphenyl) ether; bis (4-hydroxyphenyl) sulfide, bis (4-hydroxy-3-) Bis (4-hydroxyphenyl) sulfides such as methylphenyl) sulfide; bis (4-hydroxy) Bis (4-hydroxyphenyl) sulfones such as dizinyl) sulfone, bis (4-hydroxy-3-methylphenyl) sulfone and bis (4-hydroxy-13-phenylphenyl) sulfone; 4,4'-dihydroxybenzo Phenonone; 9,9-bis (4-hydroxyphenyl) fluorene, 9,9_bis (4-hydroxy-3-methylphenyl) fluorene, 9,9-bis (3-ethyl-14-hydroxyphenyl) Bis (hydroxyphenyl) fluorenes such as fluorene, 9,9-bis (4-hydroxy-13-phenylphenyl) fluorene; 4,4 ''-dihydroxy-p-dihydroxy-p such as terphenyl —Ethyl phenyls; 4, 4 '''—Dihydroxy-p—Dihydroxy p, such as quarter-phenyl, etc. —Quatarfeni 2,5-bis (4—hydroxyphenyl) pyrazine, 2,5-bis (4—hydroxyphenyl) -1,3,6-dimethylvirazine, 2,5—bis (4—hydroxyphenyl) 1,2,6 —Bis (hydroxyphenyl) pyrazines such as getylvirazine; 1,8-bis (4-hydroxyphenyl) methane, 1,8—bis (4-hydroxy-13-methylphenyl) methane, 1,8 8 — Bis (4-hydroxy 3, 5-dimethylphenyl) methane and other bis (hydroxyphenyl) methanes; 1, 4-bis [2-(4-hydroxyphenyl) 1-2-propyl Benzene, 1,3- [2- (4-hydroxyphenyl) _2-propyl] benzene, etc .; dihydroxyaryl compound group (II-a) composed of a siloxane compound represented by the following general formula (V) ) Is mentioned.

(In the general formula (V), R ³ °, R ³¹ , R ³² and R ³³ each independently represent a hydrogen atom, an alkyl group such as a methyl group or an ethyl group, an aryl group such as a phenyl group, a fluorine atom, Represents a halogen atom such as a chlorine atom, X represents an integer of 0 to 20, and y represents an integer of 0 to 2000.)

 Among them, dihydroxyaryl compound (II) [dihydroxyaryl compound group (II-b)] which is preferably used includes 2,2-bis (4-hydroxyphenyl) propane and 1,1-bis (4-hydroxyphenyl) cyclo. Hexane, 1,1-bis (4-hydroxyphenyl) 1-1,1-diphenylmethane, 1,1-bis (4-hydroxyphenyl) 1-1, phenylethane, 2,2-bis (4-hydroxy-3-) Methylphenyl) propane, 2,2-bis (4-hydroxy-3-phenylphenyl) propane, 4,4'-dihydroxybiphenyl and bis (4-hydroxyphenyl) sulfone, especially 2,2-bis ( 4-Hydroxyphenyl) propane is preferably used.

 In addition to the above-mentioned dihydroxyaryl compound (II), dihydroxyxyindanes such as 6,6′-dihydroxy-1,3,3 ′, 3′-tetramethylbisindane; It is also possible to use dihydroxynaphthalenes such as evening ren, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, and 2,7-dihydroxynaphthalene. Monkey

 One of these dihydroxyaryl compounds may be used alone, or two or more thereof may be used in combination.

The polymer C of the present invention having the repeating unit (1) as a main component and having the terminal group (3) is a dihydric alcohol (I) and a monohydric alcohol represented by the following general formula (III). Polycondensation of (III) with a carbonate-forming compound such as phosgene in the presence of a suitable acid binder, or by dihydric alcohol (I) and monohydric alcohol (III) with bisaryl carbonate Such as transesterification with Can be manufactured. Rf ² -OH (III)

(In the general formula (III), R f ² has the same meaning as described above.)

 As a preferred monohydric alcohol (III), a monohydric alcohol having a structure having at least one fluorine atom at the / 3 or a position of the hydroxyl group is desirable. Examples of such preferred monohydric alcohols (III) include those represented by the following general formula.

F— (CF ₂ ) _r — CH ₂ — OH, F— (CF ₂ ) „— CHFCF ₂ CH ₂ — OH, F— (CF ₂ ) _r — (CH ₂ ) _S — 0H-

_{F- (CF 2) r O-} CF-CH 2 -OH, F- (CF 2) r - CF- CH 2 - OH, H- (CF 2) r - CH 2 - Oil,

CF ₃ CF ₃

F- (CF ₂ ) _S H- (CH ₂ ) _S H- (CH ₂ ) _s 0

F— (CF ₂ ) _r — CH— OH, F— (CF ₂ ) _r — CH— OH, F- (CF ₂ ) _r -CH-OH

(Wherein, r and s have the same meaning as described above.)

Specific examples of the above-mentioned monohydric alcohol (III) include 2,2,2-trifluoroethanol, 2.2,3,3,3-pentafluoropropanol, and 1H, 1H-perfluoropropyl alcohol. 1H, 1H-perfluoroheptanol, 1H, 1H-perfluorohepanol, 1H, 1H-perfluorohepanol, 1H, 1H-perfluorooctanol , 1 H, 1 H—perfluorononanol, 1 H, 1 H—perfluoro undecanol, 1 H, 1 H—perfluoro undecanol, 1 H, 1 H—perfluoro dodecanol, 1 H , 1 H—perfluorotride, 1 H, 1 H—perfluorotetradecanol, 1 H, 1 H—perfluoropentadecanol, 1 H, 1 H, 2 H, 2 H—perfluoropropanol, 1 H, 1 H, 2 H, .2 H—Perfluorinated, 1 H, 1 H, 2 H, 2H—Perfluorinated 1 H, 1 H, 2 H, 2 H—perfluorohexanol, 1 H, 1 H, 2 H, 2 H—perfluoroheptanol, 1 H, 1 H, 2 H, 2 H—perful Oroktanol, 1 H, 1 H, 2H, 2H—Perfluoronona Nol, 1 H, 1 H, 2 H, 2 H—Perfluorode force, 1 H 1 H, 2 H, 2 H—Perfluoroundecanol, 1 H 1 H, 2 H, 2 H—Pa 1 Fluoro dodecanol, 1 H 1 H, 2 H, 2 H—perfluoro toredecanol, 1 H, 1 H, 2 H, 2 H—Perfluorototradecanol, 1 H, 1 H, 2 H, 2 H—Perfluoropentadecanol, 7, 7, 8, 8, 8—Pentafluoro Kutanol, 77,88,9,910,10,10—Nonafluorode Power, 7,7,8,8 7, 8, 8, 9, 9, 1 0, 1 0, 1 1 1 1, 1 2 1 2, 1 2 1 Tridecafluoro dodecanol, 7, 7, 8, 8 9 9 1 0 1 0 1 1 1 1 1 2, 1 2 1 3, 1 3 1 4 1 4, 1 4—Heptadecafluoro Tetradecanol, 1 H 1 H, 3 H—Perfluorobutanol, 1 H 1 H— 2—Trifluoro Methylbutanol, 1 H, 1 H—2—Perfluoropropyloxypropanol, HI, a, ω—Trihydroper Full O b ethanol, alpha, shed, .omega.-tri arsenide drop per full O Lop ⁰ Nord, a, α, ω- Bok Li arsenide Doropafuruo b butanol, α a, ω- tri arsenide drop per full O b pentanoate - Le ,, Α, ω-trihydrodropperfluorohexanol, α, a, ω-trihydrodropperfluorohepanol, HI, α, ω-trihydrodropperfluorooctanol, HI, α , ω-trihydrodropperfluorononanol, hi, α, ω-trihydrodropperfluoronanol, hi, a, ω-trihydride. 1-fluoroundecanol, α, α, ω-trihydro-dropa 1-fluoro-dodecanol, 1 1, 1, 3 3 3 -hexafluoro 2-propanol, 1,1,1 1-trifluoro-2-propanol, 1 Η, 1 Η, 1 Η, 2 Η—perfluoro-2-pentanol, 1-methoxy 1 H—perfluoropropanol.

 Further, in addition to the monohydric alcohol represented by the above general formula, 4,4,5,5,6,6,7,7,7-nonafluoro-2-heptenol, 4,4,5,5,6,

6,7,7,8,8,9,9,9 Tridecafluoro-2-nonenone, 4,4,5.5,6,6,6,7,7,8,8,9,9,10,1 0, 1 1, 1 1, 1 1 1 heptane decafluoro-2, ndecenol, 4, 4, 5, 5, 6, 6, 6, 7, 7, 7 — nonafluoro-2-heptaheptanol, 4, 4, 5 , 5, 6, 6,

7, 7, 8 8 9, 9, 9 1 Ridecafluoro-2-iodononanol, 4, 4, 5, 5, 6, 6, 7, 7, 8, 8, 9, 9, 1 0, 10, 1 1, 1 1, 1 1 1 heptadecafluoro-2-iodoundecanol, 1 H, 1 H , 2 H, 2 H-5—Trifluoromethyl benzo-hexanol, 1 H, 1 H, 2 H, 2 H-7—Trifluoromethyl butyl fluoranol, 1 H, 1 H, 2 H, 2H—9-Trifluoromethyl-vinyl fluoride, 1 H, 1 H, 2 H, 2 H—11-Trifluoromethyl-vinyl dodecanol, 2,2-bis (Trifluoromethyl) Propanol, perfluorocyclohexylethanol, perfluorobenzoyl alcohol, perfluoro-tert-butanol and the like are preferably used.

 These monohydric alcohols (III) may be used alone or in a combination of two or more.

 The above-mentioned polymer D of the present invention having the repeating unit (2) as a main component and having a terminal group (3) comprises the above-mentioned dihydroxyaryl compound (II) and the above-mentioned monovalent alcohol (III) and phosgene. Polycondensation with a carbonate-forming compound in the presence of a suitable acid binder, or transesterification of dihydroxyaryl compound (II) or monovalent alcohol (III) with bisaryl carbonate It can be manufactured by the following method.

 The polymer E of the present invention having the repeating unit (1) and the repeating unit (2) as main components and having the terminal group (3) is the above dihydric alcohol (I) and dihydroxyaryl compound (II) And polycondensation of the above-mentioned monohydric alcohol (III) with a carbonate-forming compound such as phosgene in the presence of a suitable acid binder, or a dihydric alcohol (I), a dihydroxylyl compound ( It can be produced by a method such as transesterification reaction between II) and monovalent alcohol (III) and bisaryl carbonate.

The polymer F of the present invention having the repeating unit (1) as a main component and further having the repeating unit (4) as a branch unit is a dihydric alcohol (I) and a compound represented by the following general formula (IV). Polycondensation of the trivalent phenol (IV) and an ester-forming compound such as phosgene in the presence of a suitable acid binder, or divalent alcohol (I) and trivalent phenol (IV) Es with Bizarre Carbonate It can be produced by a method such as a tell exchange reaction.

_R 54

(In the general formula (IV), R ⁵⁴ has the same meaning as described above.)

 Specific examples of the above-mentioned trivalent phenol (IV) include 111-tris (4-hydroxyphenyl) ethane, 1,1,11-tris (4-hydroxyphenyl) phenyl, and 1,1,1-tris (4-Hydroxyphenyl) butane, 1,1,1,1-tris (4-hydroxyphenyl) pentane and the like are mentioned, and 111-tris (4-hydroxyphenyl) ethane is particularly preferable.

 The polymer G of the present invention having the repeating unit (1) and the repeating unit (2) as main components, and further having the repeating unit (4) as a branch unit, comprises the dihydric alcohol (I), Polycondensation of a dihydroxylaryl compound (II) and a trivalent phenol (IV) with a carbonate-forming compound such as phosgene in the presence of a suitable acid binder, or a dihydric alcohol (I) or a dihydroxylyl compound (II) It can be produced by a method such as transesterification between II) and trivalent phenol (IV) and bisaryl carbonate.

 The polymer H of the present invention having the repeating unit (1) as a main component, having the terminal group (3), and further having the repeating unit (4) as a branch unit, comprises the above-mentioned dihydric alcohol (I ) Polycondensation of a polyhydric alcohol (III) and a trihydric phenol (IV) with a carbonate-forming compound such as phosgene in the presence of a suitable acid binder, or a dihydric alcohol (I) It can be produced by a method such as transesterification between (III) and trivalent phenol (IV) and bisaryl carbonate.

The polymer I of the present invention having the repeating unit (2) as a main component, having the terminal group (3), and further having the repeating unit (4) as a branch unit, comprises the above-mentioned dihydroxyaryl compound ( 11 1), monohydric alcohol (III) and trivalent Phenol (IV) and a carbonate-forming compound such as phosgene are polycondensed in the presence of a suitable acid binding agent, or a dihydroxyaryl compound (11), a monovalent alcohol (III) and a trivalent phenol ( It can be produced by a method such as transesterification between IV) and bisphenol carbonate.

 The polymer J of the present invention having the repeating unit (1) and the repeating unit (2) as a main component, having the terminal group (3), and further having the repeating unit (4) as a branch unit is as described above. Of dihydric alcohol (I), dihydroxylaryl compound (11), monohydric alcohol (III) and trihydric phenol (IV) with a carbonate-forming compound such as phosgene in the presence of a suitable acid binder. Condensation or transesterification of dihydric alcohol (I), dihydroxy carboxylic compound (11), monohydric alcohol (III) and trihydric phenol (IV) with bisaryl carbonate It can be manufactured by such a method.

 In synthesizing the polymer of the present invention, a branching agent other than the above-mentioned trivalent phenol (IV) or a terminal terminating agent may be used as a branching agent as long as the object of the present invention is not hindered. It is also possible to use a terminal terminator other than the above monohydric alcohol (III).

 As the branching agent other than the above trivalent phenol (IV), trivalent or more phenol or carboxylic acid can be used.

Specific examples of such a branching agent [Branching agent group (X)] include phloroglysin, biguchigal, 4,6-dimethyl-2,4,6-tris (4-hydroxyphenyl) 1-2- Heptene, 2,4-dimethyl-2,4,6-tris (4-hydroxyphenyl) heptane, 2,6-dimethyl-1,4,6-tris (4-hydroxyphenyl) 1-3 Heptene, 1,3,5-tris (2-hydroxyphenyl) benzene, 1,3,5-tris (4-hydroxyphenyl) benzene, tris (4-hydroxyphenyl) phenylmethane, 2,2-bis (4,4-bis (4-hydroxyphenyl) cyclohexyl) propane, 2,4-bis {2- (4-hydroxyphenyl) -1-propyl) phenol, 2,6-bis (2-hydroxy) — 5-Methylbenzyl) 14-Methylphenol , 2- (4-arsenide Dorokishifue two Le) - 2 - (2, 4 dihydric Dorokishifueniru) propane, Te tetrakis (4-arsenide de Mouth xyphenyl) methane, tetrakis (4- (4-hydroxyphenylisopropyl) phenoxy) methane, 1,4-bis (4 ', 4 "dihydroxytriphenylmethyl) benzene, 2, 4 Dihydroxybenzoic acid, trimesic acid, cyanuric acid, 3,3-bis (3-methyl-1-hydroxyphenyl) -12-oxo-1,2,3-dihydroindole, 3,3-bis (4- A group of branching agents (X) such as hydroxyindole, 5-indole, 5-chloroisatin, 5,7-dichloroisatin, and 5-bromoisatin.

 Of these, phloroglysin, 1,3,5-tris (4-hydroxyphenyl) benzene and the like are preferably used.

 As the terminal terminator other than the above monohydric alcohol (III), monovalent carboxylic acids and their derivatives, and monovalent phenols can be used.

Specific examples [Terminal terminators (Y-1)] include phenol, α-naphthol, S-naphthol, o-cresole, m-cresole, p-cresol, 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol, p-ethylphenol, p-propylphenol, p-butyl Phenol, p-pentylphenol, p-hexylphenol, p-heptylphenol, p-octylphenol, p-nonylphenol, p-decylphenol, p-opendecylphenol, p-dodecylphenol, p-- Isopropylphenol, p-tert-butylphenol, 2,6-dimethyl-p-tert-butylphenol, 2-tert-pentyl-4-methylphenol, 3-methyl-1-phenol t-butyl phenol, 2-methyl-1,4-di-tert-butyl phenol, 2,4-di-tert-butyl phenol, 2,6-di-tert-butyl 4-methyl phenol, 4-tert-butyl Pentylphenol, 2,4,6-tri-tert-butylphenol, p-phenylphenol, 2,6-di-tert-butyl-4-phenylphenol, 2,6-di-sec-butyl-4-methylphenol , 0-anisole, m-anisole, p-anisole, 0-chlorophenol, m-chlorophenol, p-chlorophenol, o-bromophenol, m-bromophenol, p-bromophenol, p—Ethoxyphenol, o-aminophenol, m-aminophenol, p-aminophenol, p-cyanophenol, p-nitrophenol, 3-methyl-16-isopropylphenol, 2-methyl-5-isopropylphenol Perfluorobutanoic acid, perfluoropentanoic acid, perfluorohexanoic acid, perfluoroheptanoic acid, perfluorooctanoic acid, perfluorononanoic acid, perfluorodecanoic acid, perfluoroundecane Acids, perfluorododecanoic acid, perfluorotridecanoic acid, perfluorotetradecanoic acid, perfluoropenic decanoic acid, perfluorohexadecanoic acid, perfluorooctadecanoic acid, 2H, 2H-perfluoropentanoic acid, 2H , 2 H—perfluorohexanoic acid, 2H, 2 H—perfluoroheptanoic acid, 2 H, 2 H—perfluoro Cuthanoic acid, 2H, 2H-Perfluorononanoic acid, 2H, 2H-Perfluorodecanoic acid, 2H, 2H-Perfluoroundecanoic acid, 2H, 2H-Perfluorododecanoic acid, 2H , 2H—perfluorotridecanoic acid, 2H, 2H, 3H, 3H—perfluorohexanoic acid, 2H, 2H, 3H, 3H—perfluoroheptanoic acid, 2H, 2H, 3H , 3H—Perfluorooctanoic acid, 2 H, 2 H, 3 H, 3 H—Perfluorononanoic acid, 2 H, 2 H, 3 H, 3 H—Perfluorodecanoic acid, 2 H , 2H, 5H-perfluoropentanoic acid, 2H, 2H, 6H-perfluorohexanoic acid, 2H, 2H, 7H-perfluoroheptanoic acid, 2H.2H, 8H-perful O-octanoic acid, 2H, 2H, 9H-C. Monofluorononanoic acid, 2 H, 2 H, 10 H—perfluorodecanoic acid, 2 H, 2 H, 11 H—perfluoroundecanoic acid, 2 H, 2 H, 12 H—perfluoro dodecanoic acid, 2 H, 2H, 13H—Perfluorotridecanoic acid or their acids, rosinide,-(perfluoropentyl) phenol, p-(perfluorohexyl) phenol, p-(perfluoroheptyl) ) Phenol, p— (perfluorooctyl) phenol, p— (perfluorononyl) phenol, p— (perfluorodecyl) phenol, p— (perfluoroundecyl) phenol, p— ( Perfluoro dodecyl) phenol, p— (perfluoro redecyl) phenol, p— (perfluorotetradecyl) phenol, p— (perfluoropentadecyl) phenol, p— (perfluo) Buchiruokishi ') Fueno Le, p-(per full O b pliers Ruo carboxymethyl') phenol, p-(to Bae one Furuo opening key (Siloxy) phenol, p- (perfluorohexyloxy) phenol, p- (perfluorooctyloxy) phenol, p- (perfluorononyloxy) phenol, p- (perfluorodecyloxy) Phenol, p— (perfluoro undecyloxy) Phenol, p— (perfluoro dodecyloxy) Phenol, p— (perfluoro tridecyloxy) Phenol, p— (perfluorotetradecyloxy) Phenol, p— (perfluoro Pentadecyloxy) phenol, 4-perfluorooctyl-2,3,5,6-tetrafluorophenol, 4-perfluorononyl 2,3,5,6-tetrafluorophenol, 4-par Fluorodecyl 2, 3, 5, 6—Tetrafluorophenol, 41 perfluorounde 2,3,5.6-Tetrafluorophenol, 4-Perfluorododecyl-1,2,5,6-Tetrafluorophenol, 4-Perfluorotridecyl-2,3,5,6-Tetrafluorophenol Phenol, 4-perfluorotetradecyl-2,3,5,6-tetrafluorophenol, 4-fluoropentadecyl-2,3,5,6-tetrafluorophenol, p-tert- Perfluorobutylphenol, 3-Methyl-41-Perfluorononylphenol, p- (2- (1H, 1H-Perfluorooctyloxy) 1-1,1,1,1,3,3,3 —Hexafluoro-2-propyl) phenol, p— (2— (1H, 1H—perfluorononyloxy) 1-1,1,1,1,3,3,3—hexafluoro-2-propyl) phenol, p— (2— (1 H, 1 H—perfluorodecyloxy) 1 1, 1, 1, 3, 3,3-hexafluoro-2-propyl) phenol, p- (2- (1H, 1H-perfluoroundecyloxy) -1,1,1,1,3,3,3-hexafluoro-2 —Propyl) phenol, p— (2— (1H, 1H—perfluorododecyloxy) —1,1.1,3,3,3hexafluoro-2-propyl) phenol, 3,5-bis (perfluoro To the mouth Xyloxycarbonyl) phenol, p— (1H, 1H—perfluoropentyloxy) phenol, p— (1H, 1H—Perfluoromouth hexyloxy) phenol, p— (1H, 1H—perfluorohexyl) phenol, p— (1H, 1H—perfluorooctyloxy) phenol, p— (1H, 1H—perfluorononyloxy) phenol, p— (1 H, 1 H—Perfluoros Phenol, p— (1H, 1H—perfluoroundecyloxy) phenol, p— (1H, 1H—perfluorododesiloxy) phenol, p— (1H, 1 H—perfluorotoridylsiloxy) phenol, p—perfluoropentyl hydroxybenzoate, P—hydroxy peroxy hexyl peroxy, p—hydroxy peroxy peroxy heptyl heptyl, p—hydroxy benzoate Perfluoro acid octyl perfluoro, perfluorononyl p-hydroxybenzoate, perfluorodecyl p-hydroxybenzoate, perfluoroundecyl p-hydroxybenzoate, p-hydroxybenzoic acid Perfluorododecyl, (p-hydroxybenzyl) perfluorohexane, (p-hydroxybenzyl) perfluoroheptan, (p-hydroxybenzyl) ) Perfluorooctane, (p-hydroxybenzil) c. Monofluorononane, (p-hydroxybenzyl) perfluorodecane, (p-hydroxybenzyl) perfluoroundecane, (p-hydroxybenzyl) perfluorododecane, and the like.

 Among these, [Terminal terminators (Y-2)] include p- (tert-butyl) phenol, p-phenylphenol, p- (perfluorononinolephenyl) phenol, and p- (tert-butyl) phenol. (No, ° -phenolic), phenol, p-tert_perfluorobutylphenol, 1- (p-hydroxybenzyl) perfluorodecane, p— (2— (1H , 1H—perfluorotridecyloxy) — 1,1,1,3,3,3-hexafluoropropyl) phenol, 3,5-bis (perfluorohexyloxycarbonyl) phenol, p—h Perfluoro dodecyl doxybenzoate, P_ (1H, 1H-perfluorooctyloxy) phenol, 2H, 2H, 9H-Terminal terminator such as perfluorononanoic acid (Y- 2).

 A preferable range of the total amount of the terminal stopper is 0.01 to 30 mol%, more preferably 1 to 1 Omo 1%, as a copolymer composition ratio. 3 If Omo is more than 1%, the surface hardness is insufficient and it is liable to wear due to insufficient surface durability, and if it is less than 0.01mol%, the solution viscosity increases, making it difficult to manufacture the photoconductor by the liquid coating method. There is.

A preferable range of the total amount of the branching agent is 0.01 to 30 mol%, more preferably 1 to 10 mol% as a copolymer composition ratio. Less than 0.01% mo 1% Feet easily wear and shorten the printing life. If it exceeds 3 Omo 1%, the solution viscosity increases, and it may be difficult to manufacture the photoconductor by the liquid coating method.

 The terminating agent and the branching agent are used in coexistence with the above-mentioned various raw material monomers. As a method, the reaction is carried out by coexisting with the dihydric alcohol (I) and / or the dihydroxylyl compound (II) from the beginning. A method of producing an oligomer comprising a divalent alcohol (I) and / or a dihydroxyaryl compound (II), and then coexisting both when producing a high molecular weight; and a method of producing a high molecular weight. After preparing an oligomer comprising (I) and a di- or dihydroxyaryl compound (II), a method is used in which a terminal terminator is allowed to coexist with the oligomer to react with the oligomer, and then a branching agent is co-present to increase the molecular weight. , A dihydric alcohol (I) and an oligomer consisting of Z or a dihydroxyaryl compound (II), and then add a branching agent to the oligomer first. By presence reacted with Origoma, then allowed to coexist terminating agent can be employed methods such as various methods of molecular weight.

 The reaction of performing polycondensation in the presence of an acid binder using a variety of carbonyls such as the above-mentioned phosgene as the carbonate-forming compound, haloformates such as chloroform, carbonate compounds, and the like, Usually, it is carried out in a solvent. When a gaseous carbonate-forming compound such as phosgene is used, a method of blowing it into the reaction system can be suitably employed.

 The proportion of the carbonate-forming compound used may be appropriately adjusted in consideration of the stoichiometric ratio (equivalent) of the reaction.

 Examples of the acid binder include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, organic bases such as pyridine and mixtures thereof. Are used.

The proportion of the acid binder used may be appropriately determined in consideration of the stoichiometric ratio (equivalent) of the reaction. Specifically, 2 equivalents or an excess amount, preferably 2 to 1 equivalent, of the total number of moles of the dihydric alcohol (I) and the dihydroxyaryl compound (II) to be used (1 mole usually corresponds to 2 equivalents). It is preferable to use 10 equivalents, or 3 equivalents or an excess amount, preferably 3 to 10 equivalents, of the acid binding agent with respect to 1 mol of the trivalent phenol (IV). As the solvent, various solvents such as those used in the production of known polycarbonates may be used alone or as a mixed solvent. Representative examples include, for example, hydrocarbon solvents such as toluene and xylene, and halogenated hydrocarbon solvents such as methylene chloride, chloroform, and benzene. The interfacial polycondensation reaction may be performed using two kinds of solvents that do not mix with each other. Further, in order to promote the polycondensation reaction, it is desirable to carry out the reaction by adding a catalyst such as tertiary amine or quaternary ammonium salt such as triethylamine. If desired, a small amount of an antioxidant such as sodium sulfite or hydrosulfide may be added. The reaction is usually carried out at a temperature in the range of 0 to 150 ° C, preferably 5 to 40 ° C. The reaction pressure can be any of reduced pressure, normal pressure, and pressurized pressure, but usually, it can be suitably performed at normal pressure or about the self-pressure of the reaction system. The reaction time depends on the reaction temperature and the like, but is usually 0.5 minutes to 10 hours, preferably about 1 minute to 2 hours.

 First, an oligomer is formed by reacting a dihydric alcohol (I) and Z or a dihydroxyaryl compound (II) and, if necessary, a part of the reaction material comprising the branching agent with a carbonate-forming substance. Then, a two-stage method in which the remaining reaction materials are added to complete the polycondensation can also be used. According to such a two-step method, the control of the reaction is easy and the molecular weight control with high accuracy can be performed.

 The latter dihydric alcohol (I) and / or dihydroxyaryl compound (11), and bisaryl carbonate used in the transesterification method of the above-mentioned branching agent or terminal terminator with bisaryl carbonate, which may be used as the case may be. Examples thereof include di-p-tolyl carbonate, phenyl-p-tolyl carbonate, di-p-toluene phenyl carbonate, and dinaphthyl carbonate.

As a reaction mode of the transesterification method, a melt polycondensation method, a solid phase polycondensation method, and the like are suitable. When performing the melt polycondensation method, dihydric alcohol (I) and Z or dihydroxyaryl compound (11), and optionally the above-mentioned branching agent or terminal terminator, and bisaryl carbonate are mixed, Melting at high temperature under reduced pressure React in the state. The reaction is usually carried out at a temperature in the range from 150 to 350 ° C, preferably from 200 to 300 ° C. When the solid-phase polycondensation method is performed, dihydric alcohol (I) and Z or dihydroxyaryl compound (11), and optionally the above-mentioned branching agent or terminal terminating agent, and bisaryl carbonate are mixed. In the solid state, polycondensation is performed by heating to a temperature lower than the melting point of the produced polycarbonate. In any case, at the final stage of the reaction, the degree of reduced pressure is preferably adjusted to 1 mmHg or less, and the funinols derived from the bisaryl carbonate produced by the transesterification are distilled out of the system. The reaction time depends on the reaction temperature and the degree of pressure reduction, but is usually about 1 to 4 hours. The reaction is preferably carried out in an atmosphere of an inert gas such as nitrogen or argon, and the reaction may be carried out by adding the above-mentioned molecular weight regulator, antioxidant or the like, if desired.

 The reduced viscosity of the obtained polymer can be adjusted to the above range by various methods such as selection of the reaction conditions and adjustment of the amounts of the branching agent and the terminal stopper. In some cases, the obtained polymer is appropriately subjected to physical treatment (mixing, fractionation, etc.) and / or chemical treatment (polymer reaction, cross-linking treatment, partial decomposition treatment, etc.) to obtain a polymer having a predetermined reduced viscosity. It can also be obtained as a union.

 [3] Resin coating liquid

 Further, the present invention provides a resin coating solution comprising the above-mentioned polymer of the present invention, a charge transport substance and a solvent.

 The polymer of the present invention has good compatibility with various charge transporting substances, and does not cause whitening or gelation even when dissolved in various solvents. Therefore, the resin coating solution of the present invention containing the polymer, the charge transport substance and the solvent can be stably stored over a long period of time without causing whitening or gelling of the polymer component. . When a photosensitive layer of an electrophotographic photoreceptor is formed using this resin coating solution, an excellent electrophotographic photoreceptor that does not cause crystallization of the photosensitive layer and does not produce image quality-like diffuses can be produced. Can be.

As the ratio of the polymer and the solvent in the resin coating solution of the present invention, the ratio of the polymer to the total amount of the polymer and the solvent is usually 1 to 30% by weight, preferably 5 to 20% by weight. it is desirable that the weight _^0/0. Also, the polymer and the charge transport material in the resin coating solution The ratio is usually 20:80 to 80:20, preferably 30:70 to 70:30 by weight.

 In the resin coating liquid of the present invention, the polymer of the present invention may be used alone or in combination of two or more.

 In addition, a resin known as a binder resin in the electrophotographic photoreceptor can be used in combination as long as the object of the present invention is not hindered. Such a resin will be described in detail later in the description of the electrophotographic photoreceptor of the present invention.

 Examples of the solvent include aromatic solvents such as benzene, toluene, xylene, and benzene, ketones such as acetone, methyl ethyl ketone, and cyclohexanone; alcohols such as methanol, ethanol, and isopropanol; ethyl acetate; Esters such as ethyl sorb, carbon tetrachloride, chloroform, halogenated hydrocarbons such as dichloromethane and tetrachloroethane, ethers such as tetrahydrofuran and dioxane, dimethylformamide, dimethylsulfoxide, getylformamide, etc. Can be suitably used.

 One of these solvents may be used alone, or two or more thereof may be used as a mixed solvent.

 The charge transport material used in the resin coating solution of the present invention will be described in detail in the description of the electrophotographic photoreceptor of the present invention described later. In addition, the resin coating liquid may contain only one kind of the charge transporting substance, or may contain two or more kinds of the charge transporting substance.

 Further, various additives can be added to the resin coating liquid of the present invention, if necessary, in order to improve the performance of a photosensitive layer formed using the liquid. Details of such an additive will be described later in the description of the electrophotographic photosensitive member of the present invention.

The resin coating liquid of the present invention is generally suitably used for forming a charge transport layer of a laminated electrophotographic photosensitive member in which a photosensitive layer contains at least a charge generation layer and a charge transport layer. In addition, when the above resin coating solution further contains a charge generating substance, it can be used for forming a photosensitive layer of a single-layer type electrophotographic photosensitive member. The charge generating substance that can be used in the resin coating liquid of the present invention will be described in detail later in the description of the electrophotographic photoreceptor of the present invention. [4] Electrophotographic photoreceptor

 The present invention further provides an electrophotographic photoreceptor having a photosensitive layer containing a charge generating substance, a charge transporting substance and a binder resin on a conductive substrate, wherein the photosensitive layer serves as a binder resin. An object of the present invention is to provide an electrophotographic photosensitive member characterized by using a combination.

 The electrophotographic photoreceptor of the present invention contains at least one of the above polymers as a binder resin, a charge generating substance and a charge transporting substance in a photosensitive layer.

 The structure of the electrophotographic photoreceptor of the present invention is not particularly limited as long as such a photosensitive layer is formed on a conductive substrate, and various types of known types such as a single layer type and a laminated type are known. Any type of photoconductor can be used, but the binder of the charge transport layer in the multilayer electrophotographic photoconductor has at least one charge generation layer and at least one charge transport layer. It is preferably used as one resin.

 In the electrophotographic photoreceptor of the present invention, the above-mentioned polymer may be used alone as a binder resin, or may be used in combination of two or more. Further, if desired, other resin components such as polycarbonate may be contained as long as the object of the present invention is not hindered.

 As the material of the conductive substrate used for the electrophotographic photoreceptor of the present invention, various materials such as known materials can be used, and specifically, aluminum, nickel, chromium, palladium, titanium, gold, silver , Copper, zinc, stainless steel, molybdenum, indium, platinum, brass, lead oxide, tin oxide, indium oxide, ITO or graphite plates, drums and sheets, and coating by vapor deposition, sputtering, coating, etc. Glass, cloth, paper or plastic film, sheet and seamless belt, plastic film laminated with metal foil such as aluminum, sheet and seamless belt, and metal sheet film sheet and seamless belt , And metal oxidation treatment by electrode oxidation etc. A metal drum or the like can be used.

The charge generation layer of the multi-layer type electrophotographic photoreceptor contains at least a charge generation substance, and the charge generation layer is deposited on a substrate as an underlayer by vacuum deposition, sputtering, or CVD. It can be obtained by forming a layer of the charge generating substance by the method described above, or by forming a layer in which the charge generating substance is bound using a binder resin on the underlying layer. Various methods such as a known method can be used as a method for forming the charge generation layer using a binder resin. Usually, for example, a coating method in which a charge generation material is dispersed or dissolved in a suitable solvent together with a binder resin. A method of applying the liquid on a predetermined base layer and drying the liquid is preferably used.

As the charge generating substance, various substances such as known substances can be used. Specifically, amorphous selenium, selenium alone such as trigonal selenium, tellurium alone, selenium-tellurium alloy, selenium alloy selenium such as boron alloy, selenium compounds such as a s ₂ S e ₃ or selenium-containing compositions, zinc oxide, sulfide mosquito domitroban um, sulfide antimony, zinc sulfide, alloys such as C d S- S e, the Various inorganic materials such as inorganic materials composed of elements from Group II and Group 16 elements, oxide-based semiconductors such as titanium oxide, and silicon-based materials such as amorphous silicon, metal-free phthalocyanine, and metal-free phthalocyanine Metal-free phthalocyanine pigments, α-type copper phthalocyanine, / 3-type copper phthalocyanine, 7-type copper phthalocyanine, ε-type copper phthalocyanine, X-type copper phthalocyanine, A-type titanyl phthalo Anine, B-type titanyl phthalocyanine, C-type titanyl phthalocyanine, D-type titanyl phthalocyanine, E-type titanyl phthalocyanine, F-type titanyl phthalocyanine, H-type titanyl phthalocyanine, G-type titanyl phthalocyanine, K-type titanyl Metallic phthalocyanines, such as rufcy-cythocyanine, L-type titanyl phthalocyanine, M-type titanyl phthalocyanine, N-type titanyl phthalocyanine, and titanyl phthalocyanine that show a strong diffraction peak at a black angle of 27.3 ± 0.2 degrees in the X-ray diffraction diagram Pigments, cyanine dyes, anthracene pigments, bisazo pigments, pyrene pigments, polycyclic quinone pigments, quinacridone pigments, indigo pigments, perylene pigments, pyrylium dyes, thiapyrylium dyes, polyvinyl carbazole, squarium pigments, anthane pigments Toguchi pigment Benzimidazole pigments, azo pigments, thioindigo pigments, bisbenzoymidazole pigments, quinoline pigments, lake pigments, oxazine pigments, dioxazine pigments, triphenyl methane pigments, azurenium dyes, squarium dyes, triaryl methane dyes, Xanthine dyes and thiazine dyes are exemplified. For example, a compound represented by the following general formula is preferably used,

[Wherein, Z ', ZZ ³ and Z ⁴ each independently have a substituent and may form an aromatic hydrocarbon ring or a heterocyclic ring together with two carbon atoms on the pyrrole ring. And M represents two hydrogen atoms or a metal atom or a metal compound which may have a ligand. ]

Ar ⁶ 4N2 N— Cp

[Wherein, Ar ⁶ represents a t-valent residue having a conjugated system which may contain an aromatic hydrocarbon ring or a heterocyclic ring, t is a positive number of 1 or more, and C p is Represents a coupler residue having an aromatic hydroxyl group, and when t is 2 or more, each C p may be the same or different. ]

[Where X ² , X ³ , X ⁴ and X ⁵ are each! R ¹⁶ and R ′ ⁷ represent an alkyl group or an aryl group having 1 to 12 carbon atoms, and represent X ² or X ³ and R ¹⁶ And X ⁴ or X ⁵ and R ¹⁷ may form a heterocyclic ring which may have a substituent. ]

O/sefcvIDd O The following are examples of fluorene-based disazo pigments.

O / sefcvIDd O

One

609Z0 / S6df / X3d S61 / 96 OW Examples of perylene pigments include the following,

ε one

609Z0 / S6dT / X3d S61 / 96 OAV Examples of polycyclic quinone pigments include the following <

,

The following are examples of the anthrone pigments.

ジベンズピレンキノン顔料としては、 以下のような例がある。 (CN) 9

Examples of the dibenzpyrene quinone pigment are as follows.

ピラン トロン顔料としては、 以下のような例がある,

Examples of pyranthrone pigments include the following,

These pigments can be used alone or in combination of two or more.

The thickness of the charge generation layer is preferably from 0.01 to 2.0 m, more preferably from 0.1 to 0.8 / m. If it is less than 0.01 m, the charge generation layer should be formed uniformly When it exceeds 2.0 m, the electrophotographic properties tend to decrease. The binder resin used for the charge generation layer is not particularly limited, and various resins such as known resins can be used. Specifically, polystyrene, polyvinyl chloride, polyvinyl acetate, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, alkyd resin, acrylic resin, polyacrylonitrile, and polycarbonate Polyurethane, epoxy resin, phenol resin, polyamide, polyketone, polyacrylamide, butyral resin, polyester, vinylidene chloride-vinyl chloride copolymer, methacrylic resin, polystyrene, styrene-butadiene copolymer, chloride Vinylidene-acrylonitrile copolymer, vinyl chloride monovinyl acetate-water-free maleic acid copolymer, silicone resin, silicone-alkyd resin, phenol-formaldehyde resin, styrene-alkyd resin, poly — N-vinyl carbazole, polyvinyl Tylal, polyvinyl formal, polysulfone, casein, gelatin, polyvinyl alcohol, ethyl cellulose, nitrocellulose, carboxy-methyl cellulose, vinylidene chloride-based polymer latex, acrylonitrile-butadiene copolymer, vinyl toluene-styrene copolymer Polymer, soybean oil-modified alkyd resin, nitrated polystyrene, polymethylstyrene, polyisoprene, polycarbonate, polyarylate, polyhaloacrylate, polyallylether, polyvinylacrylate, melamine resin, Thermosetting resins such as polyester resin, benzoguanamine resin, epoxy acrylate resin, urethane acrylate resin, and polyester acrylate can be used.

 The polymer of the present invention described above can also be used as the binder resin in the charge generation layer.

 Next, the charge transport layer can be obtained by forming a layer formed by binding a charge transport material with a binder resin on a base layer (for example, a charge generation layer).

Various methods such as a known method can be used as a method for forming the charge transport layer. Usually, a coating solution in which the above-described charge transporting substance is dispersed or dissolved in a suitable solvent together with the polymer of the present invention, for example, the above-mentioned resin coating solution of the present invention is used as a predetermined base. A method is used in which the composition is applied on a layer and dried. The compounding ratio of the charge transport material to the polymer of the present invention in the charge transport layer is preferably 20:80 to 80:20, more preferably 30:70 to 70: 3 by weight. It is 0.

 In the charge transport layer, the polymer of the present invention can be used alone or as a mixture of two or more. In addition, other resins such as those mentioned as the binder resin used in the charge generation layer can be used in combination with the polymer of the present invention as long as the object of the present invention is not hindered.

 As the charge transport substance, various substances such as known substances can be used. For example, levazole compounds, indole compounds, imidazole compounds, oxazole compounds, pyrazole compounds, oxadiazole compounds, pyrazoline compounds, thiadiazole compounds, aniline compounds, hydrazone compounds, aromatic amine compounds, aliphatics Amine compounds, stilbene compounds, fluorenone compounds, quinone compounds, quinodimethane compounds, thiazole compounds, triazole compounds, imidazo compounds, imidazolidine compounds, bisimidazolidine compounds, oxazo compounds, benzothiazole compounds , Benzimidazole compounds, quinazoline compounds, benzofuran compounds, acridine compounds, phenazine compounds, poly-N-vinylcarbazole, polyvinylvinylene, polyvinylant Styrene, polyvinyl acridine, poly 9-vinyl phenylanthracene, pyrene-formaldehyde resin, ethylcarbazole resin, or a polymer having these in the main chain or side chain is preferably used. A compound represented by the formula is used.

N

 / \

 Ar 2 Ar

Wherein, A i "', A r 2 , and A r ³ are each independently a substituted or unsubstituted alkyl group of from 1 to 1 0 carbon atoms, a substituted or unsubstituted Ararukiru group 7-1 3 carbon atoms A substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group, a heterocyclic group, a polycyclic heterocyclic group or it represents a condensed polycyclic heterocyclic group, form a ring in eight 1 "'and the 1 ~ ^2, a r ² and a r ³ and a r ³ a r' It may be. ]

[Wherein, R ′, R ² , R ³ and R each independently represent a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxyl group, a nitrile group, an amino group, an alkylamino group, or an arylamino group. Aralkylamino group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, substituted or unsubstituted aryl group having 6 to 12 carbon atoms A, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group, a heterocyclic group, a polycyclic heterocyclic group or a fused polycyclic heterocyclic group; b, c and d are each independently an integer of 0-5. ]

Wherein, A r ¹ and A r ² are each independently a hydrogen atom, the number of 1-1 0 substituted or carbon: the unsubstituted alkyl group, the number of carbon atoms? Substituted or unsubstituted aralkyl group having 1 to 13 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic ring Represents a formula group, a polycyclic heterocyclic group or a condensed polycyclic heterocyclic group, and Ar ¹ and Ar ² may form a ring. R ¹ is a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxy group, a nitro group, an amino group, an alkylamino group, an arylamino group, an aralkylamino group, a substituted or unsubstituted group having 1 to 10 carbon atoms. Alkyl group, substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic Represents a hydrocarbon group, a heterocyclic group, a polycyclic heterocyclic group or a condensed polycyclic heterocyclic group, and R ⁵ represents an ethylene group or an ethenylene group. And e is an integer from 0 to 4. ]

Wherein, A r ¹ and A r ² are each independently a hydrogen atom, a substituted young properly unsubstituted alkyl group of from 1 to 1 0 carbon atoms, a substituted or unsubstituted Ararukiru group 7-1 3 carbon atoms A substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group, a heterocyclic group, a polycyclic heterocyclic group Alternatively, it represents a condensed polycyclic heterocyclic group, and Ar ¹ and Ar ² may form a ring. R ¹ is a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxyl group, a nitro group, an amino group, an alkylamino group, an arylamino group, an aralkylamino group, and a carbon number of 1 to

A substituted or unsubstituted alkyl group having 10 to 13 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, substituted Or an unsubstituted condensed polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group or condensed polycyclic heterocyclic group, wherein R ⁶ and R ⁷ are each independently a hydrogen atom Represents an alkyl group having 1 to 6 carbon atoms or a halogen atom, and e is an integer of 0 to 4. ] l

Wherein, A r ', to ^{A r 2, A r 3,} A r 4 and A r ⁵ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1-1 0, C 7 -C 13 substituted or unsubstituted aralkyl group, 6 to 12 carbon atoms, substituted or unsubstituted aralkyl group, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic group Represents a polycyclic heterocyclic group or a condensed polycyclic heterocyclic group, wherein Ar ⁶ and Ar ⁷ are each independently a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms or 6 carbon atoms. 1 to 12 substituted or unsubstituted aryl compounds, polycyclic hydrocarbons, substituted or unsubstituted fused polycyclic Represents a divalent residue of the formula hydrocarbon, heterocyclic compound, polycyclic heterocyclic compound or condensed polycyclic heterocyclic compound, and Ar ¹ and Ar ² and Ar ³ and Ar ⁴ form a ring. You may. ]

_{^{(R 9) f (R 8}} ) Bruno _{€ ε}

 Ari

 /

 \ Ar2

Wherein, A r ', A r 2 , A r 3 and A r ⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of from 1 to 1 0 carbon atoms, the number of carbon atoms? Substituted or unsubstituted aralkyl group having 13 to 13 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic ring Shikimoto represents a polycyclic-based composite heterocyclic radical, or a condensed polycyclic heterocyclic璟式group, a r 'and a r ² and AI · ³ and a r ⁴ may form a ring. R ⁸ and R ⁹ each independently represent a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxy group, a nitro group, an amino group, an alkylamino group, an arylamino group, an aralkylamino group, a carbon number of 1 to 1 0 substituted or unsubstituted alkyl group, 7 to 13 carbon atoms, substituted or unsubstituted aralkyl group, 6 to 12 carbon atoms, substituted or unsubstituted aryl group, polycyclic hydrocarbon group, substituted or unsubstituted Represents an unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group or fused polycyclic heterocyclic group, and e and f each independently represent an integer of 0 to 4. . ]

^{Wherein, A r ', A r 2} , A r 3 and A r ⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group of from 1 to 1 0 carbon atoms, substituted carbon atoms 7-1 3 Or unsubstituted aralkyl group, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic Represents a systemic cyclic group or a condensed polycyclic heterocyclic group, and 8 1 "'and 1" ² and 1 " ³ and 8 1" ⁴ may form a ring. R ′, R ² and R ³ each independently represent a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxyl group, a nitro group, an amino group, an alkylamino group, an arylamino group, an aralkylamino group, and a carbon number of 1 to 10 substituted or unsubstituted alkyl group, substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, charcoal A substituted or unsubstituted aryl group having 6 to 12 primes, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group, a heterocyclic group, a polycyclic heterocyclic ring Represents a formula group or a fused polycyclic heterocyclic group, and e, f and g are each independently an integer of 0 to 4. X ¹ is — 0-, one S-, one S e-, one T e-, -CR ¹⁰ R "-,-S i R ^{, 0} R"-. One NR '. — Or one PR ^1G — (wherein R ′. And R ¹¹ are each independently a hydrogen atom, a halogen atom, an alkylamino group, an arylamino group, an aralkylamino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. A substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group Represents a heterocyclic group, a polycyclic heterocyclic group or a condensed polycyclic heterocyclic group. ]

[Wherein A i "i and Ar ² are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, A substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group, a heterocyclic group, a polycyclic heterocyclic group, or Represents a fused polycyclic heterocyclic group, and Ar ′ and Ar ² may form a ring, and R ′ is a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxyl group, a nitro group, Amino group, alkylamino group, arylamino group, aralkylamino group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, 6 to carbon atoms 12 substituted or unsubstituted aryl group, polycyclic hydrocarbon group, substituted or unsubstituted Or an unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group or fused polycyclic heterocyclic group, and a is an integer of 0 to 5.]

^{Wherein, A r ', A r 2} , A r \ A r and A r ⁵ each independently represent a hydrogen atom, the number of carbon atoms A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, Represents a substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group or fused polycyclic heterocyclic group, wherein R ¹ and R ² each independently represent a cyano group; A halogen atom, a carboxyl group, an acyl group, a hydroxy group, a nitro group, an amino group, an alkylamino group, an arylamino group, an aralkylamino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. A substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group , Heterocyclic group, polycyclic heterocyclic ring It represents a group or a condensed polycyclic heterocyclic group, A r 'and A r ² and A r ³ and A may form a ring. f and e are each independently an integer of 0-4. ]

[Wherein, Ar ¹ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms. Or an unsubstituted aryl group, polycyclic hydrocarbon group, substituted or unsubstituted condensed polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group or condensed polycyclic heterocyclic ring Wherein R ′, R ² and R ³ each independently represent a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxyl group, a nitrile group, an amino group, an alkylamino group, or an arylamino group. , An aralkylamino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms Group, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon Represents a hydrogen group, a heterocyclic group, a polycyclic heterocyclic group or a condensed polycyclic heterocyclic group, wherein n is 0 or 1, and a, b and c are each independently an integer of 0 to 5. ]

Wherein, A r ', A r ^2, and A r ³ are each independently a hydrogen atom, substitution or unsubstituted alkyl group having a carbon number of 1-1 0, 7 carbon atoms 1 3 substituted or unsubstituted Substituted aralkyl group, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group Represents a cyclic group or a condensed polycyclic heterocyclic group, and R ′ and R ³ each independently represent a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxy group, a nitro group, an amino group, or an alkylamino group. Group, arylamino group, aralkylamino group, substituted or unsubstituted aralkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, substituted or unsubstituted having 6 to 12 carbon atoms Substituted aryl groups, polycyclic hydrocarbon groups, substituted Represents an unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group or fused polycyclic heterocyclic group, and R ² ′ represents a hydrogen atom, a cyano group, a halogen atom, Carboxyl group, acyl group, hydroxy group, nitro group, amino group, alkylamino group, arylamino group, aralkylamino group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group Represents a heterocyclic group, a polycyclic heterocyclic group or a condensed polycyclic heterocyclic group, wherein n is 0 or 1, e is an integer of 0 to 4, and h is an integer of 0 to 3. ]

Ar ¹

/

[Wherein, AI " ¹ and Ar ² are each independently a hydrogen atom, a hydrogen atom, Substituted or unsubstituted alkyl group, substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms, polycyclic hydrocarbon group, substituted or unsubstituted Represents a substituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group or fused polycyclic heterocyclic group, and Ar ¹ and Ar ² may form a ring. ]

Ar ³

Wherein, A r A r ² and A r ³ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of 1-1 0, a substituted or unsubstituted Araruki Le carbon number 7-1 3 A substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a polycyclic hydrocarbon group, a substituted or unsubstituted fused polycyclic hydrocarbon group, a heterocyclic group, a polycyclic heterocyclic group or Represents a fused polycyclic heterocyclic group, and A r ′ and A r ² may form a ring. ]

[Wherein, R ′, R ² , R ³ , RR ⁸ and R ⁹ each independently represent a cyano group, a halogen atom, a carboxyl group, an acyl group, a hydroxyl group, a nitro group, an amino group, an alkylamino group. An arylamino group, an aralkylamino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 12 carbon atoms. An unsubstituted aryl group, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic heterocyclic group or mixed polycyclic heterocyclic group; And a, b, c, d, i and j are each independently an integer of 0 to 5. ] Ar Ar ¹

C2 CH ~ <Ar ⁶ ^ ~ CH =

Ar ⁿ \ Ar ²

Wherein, A r ', A r A to r ³ and A r ⁴ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group of from 1 to 1 0 carbon atoms, the carbon number of 7-1 3 substituted or unsubstituted Substituted aralkyl group, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic compound Ar ⁶ represents a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. Represents a divalent residue of a polycyclic hydrocarbon, a substituted or unsubstituted fused polycyclic hydrocarbon, a heterocyclic compound, a polycyclic heterocyclic compound, or a fused polycyclic heterocyclic compound, and A r ′ Ar ² and Ar ³ and Ar ⁴ may form a ring, and n is 0 or 1. ]

[Wherein, R ′ ² , R ¹³ , R ′ ⁴ and R ¹⁵ are each independently a hydrogen atom, a carbon atom having 1 to 1 (substituted or unsubstituted alkyl group, a carbon atom having 1 to 13 substituted or unsubstituted) Alkyl group, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, polycyclic hydrocarbon group, substituted or unsubstituted fused polycyclic hydrocarbon group, heterocyclic group, polycyclic system Represents a heterocyclic group or a condensed polycyclic heterocyclic group.]

Specifically, the following compounds are used.

1 one

ZO / S6dT / XJd Z 61/96 ΟΛΧ

Z / No

Z

oz

SI /

(TX f \,

^Ε Η ^{Χ Ε} Η

 01

One 09 one

CH O

609I0 / S6df / XDd

CH O

C

OC₂H₅

OC ₂ H ₅

1

N / VCH

9Z twenty five

9Z

 ¾3 /> //

 \ /

 -69-S6I / 96 OAV

609 0 / S6df / 丄 :) d CM CM

αι 〇 ϋι 〇 αι

ζι 一

609rO / S6 <U * / X3d

One £ 1

609rO / S6df / XDd ZZS6I / 96 ΟΛ Z

 VL

609I0 / S6df / X3d ZZS6I / 96 O / A o 〇 en

αι Ο ο αι

Z

Z

One 8 ー

IZS6I / 96 ΟΛ \ 09ΙΟ / 56 <ΙΓ / Χ3ί 0: / s6dT / J. DAV2 O;

,

W / no

W / no Q

w / no

W / no

Ζ

 One 08 one

Z0 / S6dT / X3d Z3S6I / 96 OAV

/19522

/ 19522

88-

 〇 in in 〇 LO

M

N—N

〇 αι

〇 αι

t t

 〇 σι

 C

 C

96/19522

96/19522

 One 94

N-N

NN

CC ₂ H ₅ ) 2 Ν ~ " ^{Ν (¾ H5) 2}

N (C ₂ H ₅ ) ₂

 ΟΖ

I 201-S61 / 96 OAVZ0 / S6df / XDd The above charge transport materials can be used alone or in combination of two or more. The thickness of the charge transport layer is preferably from 5 to 100 m, more preferably from 10 to 30. If it is less than 5 m, the initial potential will be low, and if it is more than 100 m, the electrophotographic properties tend to decrease.

 A well-known undercoat layer, which is usually used, can be provided between the conductive substrate and the photosensitive layer. For the undercoat layer, fine particles of titanium oxide, aluminum oxide, zirconia, titanic acid, zirconic acid, lanthanum lead, titanium black, silica, lead titanate, barium titanate, tin oxide, indium oxide, silicon oxide, etc. In addition, components such as polyamide resin, fuynol resin, casein, melamine resin, benzoguanamine resin, polyvinyl resin, epoxy resin, cellulose, nitrocellulose, polyvinyl alcohol, and polyvinyl butyral resin can be used. These fine particles and resins can be used alone or in combination of two or more. In particular, when fine particles are used, a resin is adsorbed on the fine particles, and a smooth film can be obtained. Further, the binder resin can be used for the undercoat layer. Further, the above-mentioned polymer of the present invention can also be used. The thickness of the undercoat layer is usually from 0.01 to 10.0 m, preferably from 0.01 to 1.0 m. If the thickness is less than 0.01 m, it is difficult to form the undercoat layer uniformly, and if it exceeds 10.0 m, the electrophotographic properties may be degraded.

 In addition, a known blocking layer, which is generally used, can be provided between the conductive substrate and the photosensitive layer. The binder resin can be used for the blocking layer. The thickness of the blocking layer is usually from 0.01 to 20.m, preferably from 0.1 to 10.0 m. When the thickness is less than 0.01 / im, it is difficult to form a blocking layer uniformly, and when the thickness exceeds 20.0〃m, electrophotographic characteristics may be deteriorated.

In the electrophotographic photoreceptor of the present invention, a protective layer may be laminated on the photosensitive layer. The thickness of the protective layer can be from 0.01 to 20 and more preferably from 0.1 to 10 zm. The binder resin can be used for the protective layer. In the protective layer, the above-described charge generation material, charge transport material, additive, metal and its oxide, nitride, salt, A conductive material such as gold or carbon may be contained.

 Further, in the electrophotographic photoreceptor of the present invention, a binder, a plasticizer, a curing catalyst, a flow-providing agent, a pinhole controlling agent, and an electrophotographic sensitivity are improved in the charge generation layer and the charge transport layer in order to improve the performance. Sensitizers (sensitizing dyes) for sensitization, apart from the spectral sensitizers, various chemicals for the purpose of preventing an increase in residual potential, a decrease in charge potential, and a decrease in sensitivity for repeated use. Additives such as substances, antioxidants, surfactants, anti-curl agents, leveling agents and the like can be added.

 Specific examples of the binder include silicone resin, polyamide resin, polyurethane resin, polyester resin, epoxy resin, polycarbonate resin, polycarbonate resin, polystyrene resin, polymethacrylate resin, and polyacrylamide resin. , Polybutadiene resin, polyisoprene resin, melamine resin, benzoguanamine resin, polychloroprene resin, polyacrylonitrile resin, ethylcellulose resin, nitrocellulose resin, urea resin, phenol resin, phenolic resin, polyvinylbutyral resin , Formal resin, vinyl acetate resin, vinyl acetate Z vinyl chloride copolymer, polyester carbonate resin and the like. Also, heat and Z or photocurable resins can be used. In any case, there is no particular limitation as long as the resin is electrically insulating and can form a skin in a normal state.

 The binder is preferably added in an amount of 5 to 200% by weight, more preferably 10 to 100% by weight, based on the charge transporting substance. If it is less than 5% by weight, the coating of the photosensitive layer tends to be non-uniform, and the image quality tends to be poor. If it exceeds 20% by weight, the sensitivity tends to decrease and the residual potential tends to increase.

 Specific examples of the plasticizer include biphenyl, biphenyl chloride, o-terphenyl, halogenated paraffin, dimethylnaphthalene, dimethylphthalate, dibutyl phthalate, dioctyl phthalate, and diethylene glycol phthalate. Rate, triphenyl phosphate, diisobutyl adipate, dimethyl sebate, dibutyl sebate, butyl laurate, methyl phthalyl ethyl glycolate, dimethyl dimethyl alcohol phthalate, methyl naphthalene, benzophenone, propylene, polystyrene And various fluorocarbons.

Specific examples of curing catalysts include methanesulfonic acid, dodecylbenzene sulfo Acid, dinonylnaphthalenedisulfonic acid and the like.

 Examples of the fluidity-imparting agent include Modaf Michiichi and Acronal 4F.

 Examples of the pinhole controlling agent include benzoin and dimethyl phthalate.

 It is preferable that the plasticizer, the curing catalyst, the flow imparting agent, and the pinhole controlling agent are used in an amount of 5% by weight or less based on the charge transporting substance.

 增 Specific examples of infectious charges include methyl violet, crystal violet, night bleed, Victoria blue, etc., triphenylamine dyes, erythroxin, rhodamine B, rhodami. 3 R, acrylic dyes such as acrylic orange, fraosine, etc., thiazine dyes such as methylene blue and methylene green, and oxazine dyes such as capri blue and meltable. And other cyanine dyes, merocyanine dyes, styryl dyes, pyrium salt dyes, and thiopyrium salt dyes.

 An electron-accepting substance can be added to the photosensitive layer for the purpose of improving sensitivity, reducing residual potential to fatigue during repeated use, and the like.

Electron accepting substances include succinic anhydride, maleic anhydride, dibromomaleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 3-nitrophthalic anhydride, Torophthalic anhydride, pyromellitic anhydride, meritic anhydride, tetrasianoethylene, tetrasanoquinodimethane, o-dinitrobenzene, m-dinitrobenzene, 1,3,5-trie Nitrobenzene, paranitrobenzonitrile, picryl chloride, quinonchlorimid, chloranil, bromanil, benzoquinone, 2.3 , Tropoquinone, anthraquinone, 1-channel anthraquinone, ginitoroanthraquino , 412 trobenzophenone, 4, 412 benzophenone, 412 trobenzalmalone ditriol, a-di-beta-(ρ-cyanophenyl) acrylate 9-anthracenylmethylmalonditritol, 1-cyano (ρ-ditrophenyl) 1 2-1- (ρ-chlorophenyl) ethylene, 2,7-dinitrofluorenone, 2,4,7—trinitrofluorenone , 2, 4, 5, 7 — Tetrani trofluorenone, 9 1-fluorenylidene [dicyanomethylenemalononitrile], polynitro-19-fluorenylidene-1 [dicyanomethylenemalonodinitrile], picric acid, o-nitrobenzoic acid, P-nitrobenzoic acid, 3, There are compounds with high electron affinity, such as 5-dinitrobenzoic acid, pentafluor-benzobenzoic acid, 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, phthalic acid, and melitic acid.

 This electron-accepting substance may be added to either the charge transport layer or the charge generation layer, and is usually 0.01 to 200% by weight based on the charge transport substance or the charge generation substance, more preferably 0 to 50% by weight.

 In order to improve the surface properties, it is necessary to improve the surface properties by using tetrafluoroethylene resin, ethylene trifluoride ethylene resin, tetrafluoroethylene ethylene hexafluoride propylene resin, vinyl fluoride resin, fusidani vinylidene resin, and difluoride dichloride. Ethylene resins, copolymers thereof, and fluorine-based polymers may be used.

 These surface modifiers are added in an amount of 0.1 to 60% by weight, more preferably 5 to 40% by weight, based on the binder resin. When the amount is less than 0.1% by weight, surface modification such as abrasion resistance, surface durability, and decrease in surface energy is not sufficient. When the amount is more than 60% by weight, electrophotographic properties may be deteriorated.

 Examples of antioxidants include hindered phenol-based antioxidants, aromatic amine-based antioxidants, hinderedamine-based antioxidants, sulfide-based antioxidants, and organic phosphate-based antioxidants. Can be

 These antioxidants are usually added in an amount of 0.1 to 10% by weight, more preferably 0.1 to 2% by weight, based on the charge transporting substance.

n n

芳香族ァミ ン系酸化防止剤としては以下のような例がある。 Examples of the hindered phenol-based antioxidants include the following.

nn

Examples of the aromatic amine antioxidant include the following.

/ = R

O ^NH Ichi 0 ^{L "NH} - ^NH"

 (R: methyl group,

 Such as ethyl group

 Alkyl group)

Such as an ethyl group

CH ₃

NH, zCH

CH ₃ CH ₃

 C

<-NH-^ Q>-NH-CH-CH ₂ -CH-CH ₃

CH ₃

Examples of hindered amine antioxidants include the following,

CH: CH CH ₃ CH ₃

o- COCK N-CH ₃ "} -CH ₂ -N 0C0 (CH ₂ ) 33

CH ₃ CH ₃

スルフィ ド系酸化防止剤としては以下のような例がある'

Examples of sulfide antioxidants include the following:

CH ₂ CH ₂ COOC ₁₂ H ₂ 5 CH ₂ CH ₂ COOC ₁₂ H ₂₅

 /

S CH ₂ CH ₂ C00C ₁₈ H ₃ 7-

CH ₂ CH ₂ COOC ₁₄ H ₂₉

 S

(C ₁₂ H ₂₅ SCH ₂ CH ₂ C00CH ₂ ) ₄ C

CH ₂ CH ₂ C00C ₁₄ H ₂₉

CH ₃ CH ₃

 -SH

S (CHCH ₂ C00C ₁₈ H ₃₇ ), tx C

Examples of the organic phosphoric acid antioxidant include the following.

ヒンダ一ドフヱノール構造単位とヒンダ一ドアミン構造単位を分子内に有する 酸化防止剤としては以下のような例がある。

Examples of the antioxidant having a hindered phenol structural unit and a hindered amine structural unit in a molecule include the following.

これら添加剤は 1種単独で用いてもよいし、 あるいは、 2種類以上を混合する などして併用してもよい。 これらの添加剤は保護層、 下引き層、 ブロッキング層 に添加してもよい。

These additives may be used alone or in a combination of two or more. These additives may be added to the protective layer, the undercoat layer, and the blocking layer.

Specific examples of the solvent used in forming the charge generation layer and the charge transport layer Are, for example, aromatic solvents such as benzene, toluene, xylene, and chlorobenzene; ketones such as acetone, methylethylketone, and cyclohexanone; alcohols such as methanol, ethanol, and isopronoganol; Esters such as acid ethyl and ethyl cellosolve, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane and tetrachloroethane, ethers such as tetrahydrofuran and dioxane, dimethylformamide, dimethyl sulfoxide, and getyl Formamide and the like can be mentioned.

 One of these solvents may be used alone, or two or more thereof may be used as a mixed solvent.

 As a method for forming a photoreceptor, a solution obtained by dispersing or dissolving the charge generating substance, the charge transporting substance, the additive, and the binder resin in a solvent is used as a predetermined base, a dip coating method, Coating method, powder coating method, spray coating method, roll coating method, applicator coating method, spray coater coating method, bar coater coating method, roll coater coating method, dip coater coating method, doctor blade Coating using a coating method such as coating method, wire bar coating method, knife coater coating method, attritor coating method, spinner coating method, bead coating method, blade coating method, curtain coating method, etc. It can be formed by drying.

 As the dispersion method, a ball mill, an ultrasonic wave, a paint shaker, a reddible, a sand mill, a mixer, an attritor, and the like can be used.

 In a single-layer type electrophotographic photoreceptor, the photosensitive layer may use the binder resin. In addition, the above-described charge generating substance and charge transporting substance can be used for the photosensitive layer of the single-layer type photosensitive member. In order to improve the electrophotographic properties of the photosensitive layer, the above additives may be used. Further, a protective layer, an undercoat layer, and a blocking layer may be provided.

 The thickness of the single-layer type photoreceptor is usually preferably from 5 to 100 m, more preferably from 8 to 50 m. If it is less than 5 rn, the initial potential tends to decrease, and if it exceeds 50 / im, the electrophotographic properties tend to deteriorate.

The ratio of the charge generating substance in the photosensitive layer of the single-layer type electrophotographic photosensitive member to the polymer of the present invention is preferably 20:80 to 80:20, and more preferably 30: 7. 0- 60: 40. Further, the ratio by weight of the charge transporting material to the copolymer of the present invention is preferably 20:80 to 80:20, and more preferably 30:70 to 70:30. The ratio by weight of the charge generating substance: the charge transporting substance is preferably 20:80 to 70:30, more preferably 30:70 to 60:40. Further, other resins can be used together with the polymer of the present invention as long as the object of the present invention is not hindered.

 The layer constitution of the photosensitive layer of the electrophotographic photosensitive member of the present invention is preferably such that the layer containing the polymer of the present invention is a surface layer of the photosensitive layer. The electrophotographic photoreceptor of the present invention obtained in this way has a high surface hardness, is a photoreceptor that maintains excellent printing durability and good cleaning properties over a long period of time, and is a copier (monochrome, multicolor). 1, Full color; analog, digital), printer (laser, LED, liquid crystal shutter), FAX, plate making machine, etc., can be suitably used in various electrophotographic fields.

 In using the electrophotographic photoreceptor of the present invention, as the charger, corona discharge (corotron, sukotron), contact charging (charging roll, charging brush) and the like are used. Exposure is performed using a halogen lamp, a fluorescent lamp, a laser (semiconductor, He—Ne), an LED, and a photoconductor internal exposure method. In the developing step, a dry developing method such as cascade developing, two-component magnetic brush developing, one-component absolute toner developing, one-component conductive toner developing, a wet developing method, and the like are used. In the transfer step, an electrostatic transfer method such as corona transfer, roller transfer, belt transfer, a pressure transfer method, or an adhesive transfer method is used. For fixing, heat roller fixing, radiant flash fixing, oven fixing, pressure fixing and the like are used. For cleaning and static elimination, brush cleaner, magnetic brush cleaner, electrostatic brush cleaner, magnetic roller cleaner, blade cleaner, etc. are used.

 [Production method of polycarbonate]

The production method of the present invention is a method for producing a polycarbonate which is subjected to interfacial polycondensation in a mixed solution of an organic solvent insoluble in water and an aqueous solution of an alkali using a carbonate-forming compound and a dioxy compound in the presence of an aqueous solution of the aluminum. In the production method, 25 as a dioxy compound. PK _a in water is used 1 5.74 less than dihydric alcohol in C This is a method for producing polycarbonate.

As the dihydric alcohol used in the present invention, as long as the small again than pK _a is 1 5. 74 is not particularly limited, we are permitted to use various dihydric alcohols. Preferably, _a dihydric alcohol having _{a pKa} of 14 or less is used, and more preferably, a dihydric alcohol having a pKa of 12 or less is used.

pK Specific examples of _a 1 5.74 less than dihydric alcohols are, for example, 2, 2-difluoro-1, 3-propanediol, 2, 2, 3, 3-te Torafuruoro - 1, 4 one-butanediol, 2,2,3,3,4,4-hexafluoro-1,5 monopentanediol, 1H, 1H, 6H, 6H-perfluoro-1,6-hexanediol, 1H, 1H, 7 H, 7H—Perfluoro 1,7—Heptanediol, 1 H, 1 H, 8 H, 8 H—Perfluoro 1,8—octanediol, 1 H, 1 H, 9 H, 9 H—Perfluoro 1 , 9-nonanediol, 1 H, 1 H, 10 H, 10 H—perfluoro-1,10-decanediol, 1 H, 1 H, 11 H, 11 H—perfluoro-1,1,1— ゥNdecanediol, 1Η, 1Η, 12 2, 12 2-perfluoro-1,12-dodecanediol, 2,2,2-trifluoro-1,1 1ethanediol, 2,2,3,3 3-penta Fluoro 1,1,1-ethanediol, 1H-perfluoro-1,1, butanediol, 1H-perfluoro-1,1, pentanediol, 1H-perfluoro-1,1,1-hexanediol, 1 Η—perfluoro; 1,1 heptanediol, 1 H-perfluoro-1,1 monooctanediol, 1 H-perfluoro-1,1-nonanediol, 1 H-perfluoro-1,1-decanediol, 1 H-perfluoro-1,1-decanediol , 1H-perfluoro-1,1-dodecanediol, perfluoropropane-1,2,2-diol, perfluorobutane-1,2,2-diol, perfluoropentane-1,3,3-diol, perfluorodecane 1,2,2-diol, perfluorododecane-1,2,2-diol, perfluorotetradecane-1,2,2-diol, 1,3-bis (2-hydroxy-1-2-perfluoropropyl) benzene, 1,4 Mono-bis (2-hydroxy 2-perfluorodecyl) benzene;

In the method of the present invention, these dihydric alcohols may be used alone. However, two or more kinds may be used in combination.

Further, in the manufacturing method of the present invention, as Jiokishi compound, pK _a in water that definitive of the above 25 ° C in addition to 1 5.74 less than dihydric alcohols, dihydric mud Kishiariru compound (Bisufu: Nord compound) Can be used as a copolymer component.

 The dihydroxyaryl compound used as the copolymerization component is not particularly limited, and various compounds can be used. For example, a dihydroxyaryl compound represented by the following general formula (II) can be suitably used. .

(Wherein, R ⁵ °, R ⁵¹ , W, A, B, and R ⁵² and R ^{53 in} W have the same meaning as described above.)

Specific examples and preferred specific examples of R ⁵ ° and R ^{51 in} the general formula (II) are the same as those described above in the description of the polymer of the present invention.

In one CR ⁵² R ⁵³ — which is an example of W in the general formula (II), specific examples and preferred specific examples of R ⁵² and R ⁵³ are the same as those described above in the description of the polymer of the present invention. is there.

 Further, specific examples of the dihydroxyaryl compound represented by the general formula (II) include the specific examples (IIa) of the dihydroxyaryl compounds described in the description of the polymer of the present invention.

 Among them, the dihydroxyaryl compounds suitably used include the specific examples (IIb) described in the description of the polymer of the present invention.

In addition to the dihydroxyaryl compounds represented by the general formula (II), dihydroxybisindanes such as 6,6′-dihydroxy-3,3,3 ′, 3′-tetramethylbisindane; Dihydroxynaphthalenes such as dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, etc. Is also suitably used as a copolymer component.

 One of these dihydroxyaryl compounds may be used alone, or two or more thereof may be used in combination.

2 5 The ° proportions of the dihydric Dorokishiariru compound p K _a in water is represented by 1 5.74 less than dihydric alcohol with the general formula (II) in the C, of the repeating units both or we formed It is suitable to use such an amount that the proportion of the repeating unit formed from the dihydric alcohol to the total is 0.1 to 99 mol%, preferably 1 to 50 mol%.

In the production method of the present invention, the dioxy compound ( _a dihydric alcohol having a pKa in water at 25 ° C. of less than 15.74 or a dihydric alcohol represented by the general formula (II) In addition to dihydroxyaryls such as dihydroxyaryl compounds), it has an aliphatic terminal group by using a monohydric alcohol having _a pKa in water at 25 ° C of less than 15.74 as a terminal stopper. Polycarbonate can also be synthesized.

The monohydric alcohol used in the present invention, if _a pK _a one smaller again than 1 5. 74 is not particularly limited, It is permitted to use various monohydric alcohols. Preferably p K _a is 1 4 monohydric alcohol, more preferably p K _a is 1 2 the following monohydric alcohol used.

pK Specific examples of _a 1 5.74 less than monohydric alcohols, for example, 2, 2, 2-preparative Riffle O B ethanol, 2, 2, 3, 3, 3-pentamethylene full O b propanol, 1 H, 1 H—perfluorobutanol, 1 H, 1 H—perfluoropenanol, 1 H, 1 H—perfluorohexanol, 1 H, 1 H—perfluorohepanol, 1 H, 1 H—Perfluorooctanol, 1 H, 1 H—Vafluorononanol, 1 H, 1 H—Perfluorodanol, 1 H, 1 H—Perfluoroundecanol, 1 H , 1 H—perfluoro dodecanol, 1 H, 1 H—perfluoro tridecanol, 1 H, 1 H—perfluorotetradecanol, 1 H, 1 H—perfluoropentadecanol, a,, ω— Application Benefits human Doropafuru Oroetanoru, a, a, ω- door Li human mud-perf Roh Leo Rob 'Lono, ⁰ Nord ,, A, ω-Tri-dropper fluorobutanol, α, a, ω-Tri-dropper fluorobutanol Pentanol, α, ω-trihydro ヽ⁰ —Fluorohexanol, HI, α, ω Trifluorodropperfluoroheptanol, α, α 'ω-Trihydr dropperfluorooctanol, α, , ω-Tri Hydrono. -Henoleolononanol, HI, NA, ω-Tri-dropperfluoride decanol, α, ω-Tri-dropperfluorone decanol, α, α, ω-Tori-dropperfluoride dodecanol, ⁰ —Fluorocyclohexylethanol, 1 1 1 3 3 3—Hexafluoro-2-propanol, 1,1,1,1-trifluoro-2-propanol, 1Η, 1Η, 1Η, 2Η—perfluoro-2 —Pentanol, perfluoro-tert-butanol, 2-cyanone 1.1.1-trifluoro-2-propanol, 2-cyanone-1,11-trifluoro-2-butanol and the like.

 These monohydric alcohols may be used alone or in combination of two or more.

 When the above-mentioned monohydric alcohol is used as a terminal stopper, the amount of the monohydric alcohol based on the total of the dioxy compound component and the monohydric alcohol is usually 0.01 to 30 mol%, preferably 0.1 to 1 mol%. Preferably, it is 0 mol%.

Further, the present invention provides a method for producing a polycarbonate which is subjected to interfacial polycondensation in a mixed solution of an organic solvent insoluble in water and an aqueous solution of an alkali using a carbonate-forming compound and a dioxy compound in the presence of an aqueous alkali solution. in the manufacturing method, using a dihydroxy § reel compounds represented by the above following general formula (〗 I) as Jiokishi compound as a terminal capping agent is p K _a in water at 2 5 ° C less than 1 5.74 Provided is a method for producing a polycarbonate, characterized by using a monohydric alcohol.

 Specific examples and amounts of the monohydric alcohol used in this production method are the same as described above. According to this production method, an aliphatic terminal group can be easily introduced into a polycarbonate having a dihydroxylyl repeating unit by an interfacial polymerization method.

 Also in this production method, the dihydroxyaryl compound represented by the general formula (I) and the above-mentioned monohydric alcohol may be used alone or in combination of two or more.

The polycarbonate obtained by the production method of the present invention is obtained by dissolving methylene chloride in a solvent. The reduced viscosity at 20 ° C. of the solution having a concentration of 0.5 gZd1 is preferably 0.2 to 10.0 d1 / g. If the reduced viscosity is less than 0. Sdl Zg, mechanical properties such as surface hardness may be insufficient. If the reduced viscosity exceeds 10 Odl Zg, the solution viscosity of the polycarbonate increases. However, the production of polycarbonate itself becomes difficult, and the workability when using polycarbonate as a solution may be impaired. More preferably, it is 0.3 to 2. O dl / g.

 In the production method of the present invention, a commonly used terminal terminator other than the above monohydric alcohol may be used, or a polycarbonate having a branched structure or a cyclic structure may be used by using a commonly used branching agent. May be manufactured.

 Other than the above-mentioned monohydric alcohol, as a terminal terminator which can be used, monovalent carboxylic acids and derivatives thereof, monovalent phenols and the like can be used.

 Specific examples of such a terminal terminator include the group of terminal terminators (Y-1) described above for the polymer of the present invention.

 Among them, those preferably used include the group of terminal terminators (Y-2) described above for the polymer of the present invention.

 As the branching agent, trivalent or higher phenol or carboxylic acid can be used. Specific examples of such a branching agent include the branching agent group (X) described above for the polymer of the present invention.

 Among these, phloroglysin, 1,3,5-tris (4-hydroxyphenyl) benzene and the like are preferably used. In addition, a trivalent phenol represented by the above general formula (IV), for example, 1,1,1-tris (4-hydroxyphenyl) phenol and the like are also preferably used.

 The preferred range of the amount of the terminal stopper is 0.01 to 30 mol%, more preferably 1 to 1 Omo 1%, as a copolymer composition ratio.

 A preferred range of the total amount of the branching agent is 0.01 to 3 Omo]%, more preferably 1 to 1 Omo 1% as a copolymer composition ratio.

The terminal terminating agent and the branching agent are used in coexistence with the above-mentioned various starting dioxy compounds. However, there are two methods to increase the molecular weight by coexisting with the dioxin compound from the beginning to make the reaction higher, or to prepare an oligomer composed of the dioxy compound, and then coexist both when increasing the molecular weight to increase the molecular weight. Method: After preparing an oligomer composed of a dioxy compound, first reacting the oligomer with a terminator in the presence of a terminator, and then coexisting a branching agent to increase the molecular weight. After the preparation, various methods can be adopted, such as a method in which a branching agent is allowed to coexist with the oligomer to react with the oligomer, and then a terminal stopper is coexisted to increase the molecular weight.

 As the polymerization method, interfacial polycondensation may be carried out from the dioxy compound and the carbonate-forming compound in the presence of an alkali as an acid binding agent to directly increase the molecular weight, or the dioxidi compound and the carbonate may be produced in the presence of an alkali. A bishaloform oligomer, preferably a bischloroformate oligomer, of a dioxy compound is once formed from the ester-forming compound, and the interfacial polycondensation between the oligomer and the dioxodi compound is performed again in the presence of an alcohol to increase the molecular weight. A two-step method may be used. According to the latter two-step method, the reaction can be easily controlled, and the molecular weight can be controlled with high accuracy.

 Examples of the carbonate-forming compound include phosgene, bischlorocarbonate of a dioxy compound, dimethyl carbonate, dimethyl carbonate, dibutyl carbonate, and dialkyl carbonate compound such as dihexyl carbonate. Products, diphenyl carbonate, ditricarbonate, g-cresilica carbonate, dinaphthyl carbonate, bis (diphenylyl) carbonate, bisphenol A bisphenylcarbonate, bis (4 Bis (4-fluorophenyl) carbonate, bis (4-chlorophenyl) carbonate, bis (4-trifluorometylphenyl) carbonate, bis (4-cyanophenyl) carbonate, bis (4-nitrophenyl) carbonate, etc. Reel carbonate Things, methylation off We sulfonyl carbonate Natick Bok, E chill phenylalanine carbonate Natick DOO, Arukiruari one Rukabone one Bok compounds such Kishirufe alkenyl carbonate to cyclohexylene Ru preferably used.

The dioxy compound in the bischlorocarbonate of the above dioxy compound is The object is not particularly limited, usually, dihydric de port p K _a in water at 2 5 ° C above is represented by 1 5.7 4 less than dihydric alcohol, or the general formula (II) It is preferably a xyaryl compound.

Among these carbonic ester-forming compound, phosgene, a Jiokishi compounds, p K _a in water at particular 2 5 ° C expressed by 1 5.7 4 less than dihydric alcohol, or the general formula (II) It is preferable to use bischlorocarbonate ester of a dioquin compound or bis (412-trophenyl) carbonate.

 When a gaseous carbonate-forming compound such as phosgene is used, a method of blowing it into the reaction system is preferred.

 The proportion of the carbonate-forming compound used may be appropriately adjusted in consideration of the stoichiometric ratio (equivalent) of the reaction. Usually, the above-mentioned dioxy compound, monohydric alcohol, monohydric phenol, trivalent phenol used in the reaction are used. It is preferable to use 1 equivalent or more for 1 equivalent of the above fugnols.

 Examples of the alkali used in the form of an aqueous solution as the acid binding agent include alkali metal hydroxides such as sodium hydroxide, hydroxide hydroxide, sodium hydroxide, sodium carbonate and the like. Limetal carbonate or a mixture thereof is used. Alkyrie is used as an aqueous solution.

 The proportion of the alkali used as the acid binder may be appropriately determined in consideration of the stoichiometric ratio (equivalent) of the reaction. Specifically, the above-mentioned dioxy compound, monovalent alcohol, monovalent phenol, trivalent or more phenol used for the reaction is used in an amount of 1 equivalent or an excess thereof, preferably 2 to 10 equivalents. It is preferred to use an acid binder.

 In the present invention, as the polymerization solvent used for the interfacial polycondensation, any solvent can be used as long as it is inert to the reaction, is insoluble in water, and dissolves the produced polymer.

As the solvent, various solvents such as those used in the production of known polycarbonates may be used alone or as a mixed solvent. Typical examples are, for example, methylene chloride (dichloromethane), 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, chloroform, 1,1,1_1 Halogenated hydrocarbon solvents such as benzene, carbon tetrachloride, monochrome benzene, dichlorobenzene, etc .; hydrocarbon solvents such as benzene, toluene, xylene, cumene, and ethylbenzene; and ether solvents such as getyl ether. Among them, methylene chloride is preferably used.

 One of these organic solvents may be used alone, or two or more thereof may be used as a mixed solvent.

 Further, a polymerization catalyst may be used to promote the polycondensation reaction. Specific examples of the polymerization catalyst suitably used in the present invention include, for example, tertiary amines such as trimethylamine, triethylamine, tripropylamine, tributylamine, dimethylbenzylamine and triphenylamine. , N, N-dimethylaniline, pyridine, 4-dimethylaminopyridine, 4-getylaminopyridin, 4-pyrrolidinopyridine, 4-aminopyridin, 2-aminopyridin, 2-hydroxypyridin, Aromatic basic compounds such as 4-hydroxypyridine, imidazole, 2-methylimidazole, 2-dimethylaminomidazole, quinoline, tetrabutylammonium chloride, trimethylbenzylammonium bromide Quaternary ammonium salts such as ammonium hydroxide, tetramethylammonium hydroxide, hydroxide hydroxide Quaternary ammonium hydroxides such as raethylammonium, tetrabutylammonium hydroxide, trimethylbenzylphosphonium halide, tetramethylbenzylphosphonium halide, triethylbenzylphosphonium halide And quaternary phosphonium salts such as 18—crown 6, 18—benzocrown-16,15—crown-15.

These polymerization catalysts may be used alone or in combination of two or more. The amount of the polymerization catalyst, the Jiokishi compound used in the reaction, monovalent alcohol for over value Fuwenoru, trivalent or higher Fuwenoru 1 equivalent, on 1 0 ⁶ Toryo以, preferably 1 0- ^s ~ it is preferable to use l 0- ² equivalents.

 Further, if desired, a small amount of an antioxidant such as sodium sulfite, hydrosulfide, trimethylphosphoric acid, triflatin phosphoric acid and the like may be added.

The amount of the antioxidant, the Jiokishi compound used in the reaction, monovalent alcohol for over value Fuwenoru, trivalent or higher Fuwenoru 1 equivalent, 1 0 ⁶ Toryo以 It is preferable to use 10 to ⁶ to 10 to ² equivalents.

 The polymerization reaction may be performed in an atmosphere of an inert gas such as nitrogen or argon.

 The polymerization reaction is usually performed at a temperature in the range of 0 to 150 ° C, preferably 0 to 60 ° C. The reaction pressure may be any of reduced pressure, normal pressure, and pressurized pressure. Usually, the reaction can be suitably performed at normal pressure or about the self-pressure of the reaction system. The reaction time depends on the reaction temperature and the like, and is usually 0.5 minutes to 10 hours, preferably about 1 minute to 2 hours. The polymerization reaction is performed under stirring.

 Hereinafter, the present invention will be described more specifically with reference to Examples of the present invention and Comparative Examples thereof. The present invention is not limited to these Examples. Example 1

 A mixture of 2,2-bis (4-hydroxyphenyl) propane (74 g) in a 5% aqueous sodium hydroxide solution (550 ml) and methylene chloride (250 ml) were stirred and cooled. Then, phosgene gas was blown into the solution at a rate of 95 Om1 / sec for 15 minutes. Next, this reaction solution was allowed to stand and separated to obtain a methylene chloride solution of an oligomer having a degree of polymerization of 2 to 4 and having a formaldehyde group at the molecular end.

Methylene chloride was added to a methylene chloride solution (250 ml) of the obtained oligomer to make a total amount of 45 Om 1, and then 2,2,3,3,4,4-hexafluoro-1,5-pentanediol ( A solution prepared by dissolving 15 g, pK _a = l 1) in an 8% aqueous sodium hydroxide solution (150 ml) was mixed, and p-tert-butyl phenol (2. 0 g) was added. Next, while vigorously stirring this mixed solution, a 7% aqueous solution of triethylamine (2 ml) was added as a catalyst, and the mixture was stirred at 28 ° C. for 1.5 hours to carry out a reaction. After the reaction is completed, the reaction product is diluted with methylene chloride (1 liter), then twice with pure water (1.5 liter) and once with 0.01 N hydrochloric acid (1 liter). Washed twice with pure water (1 liter). Further, the organic layer was put into methanol, and the polymer was taken out.

The copolymer (PC-1) thus obtained has a high glass transition temperature (Tg). 122, the reduced viscosity ["SPZC"] of a solution of 0.5 gZd 1 in methylene chloride as a solvent was 0.42 d 1 Zg at 20. The viscosity was measured by Rigosha Co., Ltd. The viscosity was measured using a kinematic viscosity measurement device VM R-042 and an automatic viscosity improved Ubbe 1 ohde type viscometer (RM type) as a viscometer. The structure was confirmed by ¹ H-NMR (FIG. 1).

ォキソチタニウムフタロシアニン 0. 5部 （重量部、 以下同様」 、 プチラール 樹脂 5部及び塩化メチレン 1 9部をボールミルにて分散し、 この分散液を バーコ一夕一を用いて導電性基体としてのアルミニゥムを蒸着したぺッ トフィル ム上に塗工して乾燥し、 電荷発生層 （膜厚約 0. 5 /zm) とした。 電荷輸送物質 として後記の （C— 1 ) を用い、 （C— 1) 1部、 （PC— 1) 1部、 塩化メチ レン 8部の溶液を調製し、 塗工液とした。 この塗工液をアプリケーターを用いて 前記の電荷発生層上に塗布して電荷輸送層 （膜厚約 20 μπι) を形成し、 積層型 電子写真感光体を作製した。 塗工時において電荷輸送層が結晶化することはなか つた。 また、 この塗工液は、 1か月放置しても、 白濁、 ゲル化の発生は見られな かった。 + 0-CH _2- (CF ₂ ) ₃ —

0.5 parts by weight of oxotitanium phthalocyanine (parts by weight, the same applies hereinafter), 5 parts of petital resin and 19 parts of methylene chloride were dispersed in a ball mill, and this dispersion was dispersed in aluminum as a conductive substrate using a Barco overnight. Was applied on a wet film on which was vapor-deposited, and dried to form a charge generation layer (film thickness: about 0.5 / zm) Using (C-1) described later as a charge transport material, (C-1 1), 1 part of (PC-1), and 8 parts of methylene chloride were prepared as a coating solution, and this coating solution was applied to the above-mentioned charge generating layer using an applicator to transport charges. A layer (about 20 μπι in thickness) was formed to produce a laminated electrophotographic photoreceptor.The charge transport layer did not crystallize during coating. However, no cloudiness or gelation was observed.

The electrophotographic properties of the obtained electrophotographic photoreceptor were evaluated by performing a 16 kV corona discharge using an electrostatic charging tester EPA-8100 (manufactured by Kawaguchi Electric Works, Ltd.) to obtain an initial surface potential (V .), the light irradiation (1 O Lu x) after 5 seconds residual potential (V _R), halving the exposure amount (E _{l / 2)} was measured. Table 1 shows the results.

Further, the abrasion resistance of the charge transport layer was evaluated using a Suga abrasion tester NUS-ISO-3 type (manufactured by Suga Test Machine Co., Ltd.). The test conditions were evaluated by reciprocating the sample 1200 times on a 200 g weighted abraded paper and measuring the change in the decrease. Table 2 shows the results. Examples 2 and 3 A photoconductor was prepared by the same method as that of Example 1 except that the charge transport material (C-1) used in Example 1 was changed to (C-1) (C-3) described later, respectively. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. In the same manner as in Example 1, the initial surface potential (V), the light potential (10 LuX), the residual potential (V _R ) after 5 seconds, the half-life exposure (E _1/2 ), and the wear The amount of decrease in the charge transport layer was measured. The results are shown in Tables 1 and 2. Example 4

Instead of 2,23,3,4,4-hexafluoro-1,5-pentanediol (15 g) used in Example 1, 1H, 1H, 6H, 6H-perfluoro-1 , 6-Hexanediol (17 g, pK _a = 11) was used, and the same operation as in Example 1 was carried out. A copolymer having the following structure (PC-2, Tg _: 117 °) C, [7? _SP Zc] = 0.52 d 1 / g). The copolymer composition was determined by 'H-NMR (Fig. 2).

バインダー樹脂として （PC— 2) 、 電荷輸送物質として （C— 1 ) を用い、 実施例 1と同様の方法で感光体を作製した。 その際、 各塗工液は、 1か月放置し ても、 白濁、 ゲル化の発生は見られなかった。 また、 実施例 1と同様の方法で初 期表面電位 （V。） 、 光照射 （1 OLu x) 5秒後の残留電位 （V_R) 、 半減露光 量 （E_1/2) 及び摩耗による電荷輸送層の減少量を測定した。 結果を表 1及び表 2 に示す。 実施例 5及び 6 + 0 one _{CH 2 - (CF 2) 4} - CH 2 one 0-

A photoconductor was prepared in the same manner as in Example 1, except that (PC-2) was used as the binder resin and (C-1) was used as the charge transport material. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. Further, initial surface potential in the same manner as in Example 1 (V.), light irradiation (1 Olu x) after 5 seconds residual potential (V _R), half-decay exposure (E _1/2) and the charge due to wear The amount of decrease in the transport layer was measured. The results are shown in Tables 1 and 2. Examples 5 and 6

A photoconductor was prepared by the same method as that of Example 4 except that the charge transport material (C-1) used in Example 4 was changed to (C-2) (C-3), respectively. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. Example 1 In the same manner as above, the initial surface potential (V.), the residual potential (V _R ) after 5 seconds of light irradiation (1 OL ux), half-exposure (E _1/2 ), and the amount of charge transport layer decrease due to abrasion It was measured. The results are shown in Tables 1 and 2. Example 7

Instead of 2,2,3,3,4,4-hexafluoro-1,5-pentanediol (15 g) used in Example 1, 1H, 1H, 8H, 8H—perfluoro-1,8 —The same operation as in Example 1 was performed except that octanediol (23 g, pK _a = 11) was used, and a copolymer having the following structure (PC-3, T g: 114 ° C, _SP no c] = 0.57 d 1 / g). The copolymer composition ratio was confirmed by ¹ H-NMR (FIG. 3).

バインダー樹脂として （PC— 3) 、 電荷輸送物質として （C一 1 ) を用い、 実施例 1と同様の方法で感光体を作製した。 その際、 各塗工液は、 1か月放置し ても、 白濁、 ゲル化の発生は見られなかった。 また、 実施例 1と同様の方法で初 期表面電位 （V。） 、 光照射 （ 1 O Lu x) 5秒後の残留電位 （V_K 、 半減露光 量 （Έ_{1 2}) 及び摩耗による電荷輸送層の減少量を測定した。 結果を表 1及び表 2 に示す。 実施例 8及び 9

A photoconductor was prepared in the same manner as in Example 1, except that (PC-3) was used as the binder resin and (C-11) was used as the charge transport material. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. Further, initial surface potential (V.) in the same manner as in Example 1, light irradiation (1 O Lu x) residual potential after 5 seconds (V _K, half decay exposure (Έ _{1 2)} and a charge transport due to wear The amount of layer loss was measured, and the results are shown in Tables 1 and 2. Examples 8 and 9

A photoconductor was prepared by the same method as that of Example 7 except that the charge transporting material (C-11) used in Example 7 was changed to (C-2) (C-3), respectively. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _K ) after 5 seconds of light irradiation (1 OL ux), the half-exposure amount, and the decrease amount of the charge transport layer due to abrasion were measured. did. The results are shown in Tables 1 and 2. Example 10

Instead of 2,2,3,3,4,4-hexafluoro-1,5-pentanediol (15 g) used in Example 1, 4,4'-biphenol (12 g) and 2,4'-biphenol (12 g) were used. 2, 2-triflate Ruo b ethanol (1. 3 5 g, p K 3 = 1 1) the same procedure is the actual Example 1 except for using the copolymer consisting of the following structures (PC - 4 , T g: 1 4 9 ° C, to give the _{[SP Z c] = 0. 4} 3 d 1 / g). The copolymer composition ratio was confirmed by 1 H-NMR (FIG. 4).

0

0

 II

-OC-0-CH ₂ CF ₃ ) 0.03

(PC-4) A photoconductor was prepared in the same manner as in Example 1, using (PC-4) as the binder resin and (C-1) as the charge transporting material. No turbidity or gelation was observed even after standing for 5 months, and the initial surface potential (V.) and the residual after 5 seconds of light irradiation (1 OL ux) were measured in the same manner as in Example 1. The potential (V _K ), the half-exposure dose (E, ' ₂ ), and the decrease in the charge transport layer due to abrasion were measured, and the results are shown in Table 1 and Table 1. Examples 11 and 12

A photoconductor was prepared by the same method as that of Example 10 except that the charge transporting material (C-1) used in Example 10 was changed to (C-2) (C-3>), respectively. In addition, no turbidity or gelation was observed even after leaving each coating solution for one month, and the initial surface potential (V.) and light irradiation (1 OL) were obtained in the same manner as in Example 1. ux) The residual potential (V _R ) after 5 seconds, the half-life exposure (E _1/2 ), and the decrease in the charge transport layer due to abrasion are shown in Tables 1 and 2. Example 13

Instead of 2,2,3,3,4,4-hexafluoro-1,5-pentanediol (15 g) used in Example 1, 4,4'-biphenol (12 g) and 1,1 , 1,3,3,3-Tetrafluoro-2-propanol (2.2 g, pK _a = 5) except that the same operation as in Example 1 was carried out. PC- 5, T g: 1 5 0 ° C, was obtained _{[7 SP Z c?] =} 0. 4 2 d 1 / g). The copolymer composition was confirmed by ¹ H-NMR (FIG. 5).

C-5) A photoconductor was prepared in the same manner as in Example 1, except that (PC-5) was used as the binder resin and (C-11) was used as the charge transport material. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _K ) after 5 seconds of light irradiation (10 LuX), the half-life exposure (露 光, ₂ ), and the The amount of decrease in the charge transport layer was measured. The results are shown in Tables 1 and 2. Examples 14 and 15

A photoconductor was prepared by the same method as that of Example 13 except that the charge transport material (C-11) used in Example 13 was changed to (C-2) (C-3), respectively. At that time, no turbidity or gelation was observed in each coating solution even after being left for one month. Also, in the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _K ) after 5 seconds of light irradiation (10 LuX), the half-exposure dose (E ,,, ₂ ) and the wear The amount of decrease in the charge transport layer due to was measured. The results are shown in Tables 1 and 2. Example 16 In place of 2,2,3,3,4,4-hexafluoro-1,5-pentynediol (15 g) used in Example 1, 4,4′-biphenol (6 g), 2,2,2 1 The same operation as in Example 1 was carried out except that trifluoroethanol (7.8 g, pK _a = 11) and tris (4-hydroxyphenyl) ethane (2 g) were used, and the following structure was used. (PC-6, Tg: 124 ° C, [7? _SP / c] = 0.28 d1 / g) was obtained. The copolymer composition ratio was confirmed by ¹ H-NMR (FIG. 6).

バインダ一樹脂として （P C— 6) 、 電荷輸送物質として （C_ 1 ) を用い、 実施例 1と同様の方法で感光体を作製した。 その際、 各塗工液は、 1か月放置し ても、 白濁、 ゲル化の発生は見られなかった。 また、 実施例 1と同様の方法で初 期表面電位 （VJ 、 光照射 （ 1 0 L u X) 5秒後の残留電位 （V_K) 、 半減露光 量 （E ₂) 及び摩耗による電荷輸送層の減少量を測定した。 結果を表 1及び表 2 に示す。 実施例 1 7及び 1 8

A photoconductor was prepared in the same manner as in Example 1, except that (PC-6) was used as the binder resin and (C_1) was used as the charge transport material. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. Further, initial surface potential in the same manner as in Example 1 (VJ, light irradiation (1 0 L u X) residual potential after 5 seconds (V _K), half decay exposure amount (E ₂₎ and a charge transport layer due to abrasion The results are shown in Tables 1 and 2. Examples 17 and 18

A photoconductor was prepared by the same method as that of Example 16 except that the charge transport material (C-1) used in Example 16 was changed to (C-2) (C-3), respectively. At that time, no turbidity or gelation was observed in each coating solution even after being left for one month. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _R ) after 5 seconds of light irradiation (1 O Lux), the half-exposure amount (E _{l 2} ), and the charge transport due to abrasion were obtained. The amount of layer loss was measured. The results are shown in Tables 1 and 2. Comparative Example 1

The same procedure as in Example 1 was carried out using bisphenol A as a raw material, polycarbonate (reduction viscosity: 0.78 d 1 / g) composed of the following repeating units as the binder resin, and (C-1) as the charge transport material. An electrophotographic photosensitive member was manufactured. At that time, the coating liquid became cloudy on the second day, and a gel was generated. In addition, part of the charge transport layer was whitened (crystallized) during coating. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _R ) after 5 seconds of light irradiation (1 OL ux), the half-exposure dose (E,), and the charge transport layer due to abrasion. Was measured. The results are shown in Tables 1 and 2.

Comparative Example 2

A photoconductor was prepared by the same method as that of Comparative Example 1 except that the charge transport material (C-11) used in Comparative Example 1 was changed to (C-12). At that time, the stability of the coating solution and the evaluation of the finished product at the time of application were the same as in Comparative Example 1. Further, in the same manner as in Example 1, the initial potential (V .; the residual potential (V, half-reduced exposure: (E, ₂ )) after 5 seconds of light irradiation (10 Lux) and abrasion, and charge transport by abrasion The amount of layer loss was measured, and the results are shown in Tables 1 and 2. Comparative Example 3

Using bisphenol Z as a raw material and a polycarbonate composed of the following repeating units (0.84 d 1 / g) as a binder resin, and using (C-1) as a charge transport material, in the same manner as in Example 1. An electrophotographic photosensitive member was manufactured. At that time, the evaluation of the stability of the coating liquid and the crystallization during coating were the same as those in Comparative Example 1. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _R ) after 5 seconds of light irradiation (1 OL ux), the half-life exposure (E _1/2 J and the charge due to abrasion) were obtained. Measure the loss of transport layer Was. The results are shown in Tables 1 and 2.

Comparative Example 4

A photoconductor was prepared by the same method as that of Comparative Example 3 except that the charge transporting material (C-1) used in Comparative Example 3 was changed to (C-12). At that time, the evaluation of the stability of the coating liquid and the crystallization during coating were the same as in Comparative Example 1. Also, in the same manner as in Example 1, the initial surface potential (V.), light irradiation (10 LuX), residual potential (V _R ) after 5 seconds, half-exposure (E _1/2 ), and wear The amount of decrease in the charge transport layer due to was measured. The results are shown in Tables 1 and 2.

table 1

Table 2

Example 19

Instead of 2,2,3,3,4-hexafluoro-15-pentanediol (1.5 g) used in Example 1, 1H, 1H6H, 6H-perfluoro-16-hexanediol (1 6 g pK _a = ll) and 2 2,2-tris (4-hydroxyphenyl) ethane (0.3 g) were used, and the same operation as in Example 1 was carried out to obtain a copolymer having the following structure (PC-7 Tg _: 1 23 ° CC] = 0.86 d 1 / g). The copolymer composition ratio was confirmed by 'H-NMR (FIG. 7).

バインダー樹脂として （PC— 7) 、 電荷輸送物質として （C— 2) を用い、 実施例 1と同様の方法で感光体を作製した。 その際、 各塗工液は、 1か月放置し ても、 白濁、 ゲル化の発生は見られなかった。 また、 実施例 1と同様の方法で初 期表面電位 （V。） 、 光照射 （ 1 O L u x) 5秒後の残留電位 （V_R) 、 半減露光 量 （E, ₂) 及び摩耗による電荷輸送層の減少量を測定した。 結果を表 3及び表 4 に示す。 実施例 20

A photoconductor was prepared in the same manner as in Example 1, except that (PC-7) was used as the binder resin and (C-2) was used as the charge transport material. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. Further, initial surface potential in the same manner as in Example 1 (V.), light irradiation (1 OL ux) after 5 seconds residual potential (V _R), the charge transport by half decay exposure amount (E, ₂₎ and wear The amount of layer loss was measured. The results are shown in Tables 3 and 4. Example 20

2,2-bis (4-hydroxyphenyl) prono used in Example 1. 1,1-bis (4-hydroxyphenyl) cyclohexane (87 g), 2,2,3,3,4,4,1-hexafluoro-1,5-pentene Instead of all (15 g), 1,1-bis (4-hydroxyphenyl) cyclohexane (15 g), 1H instead of p-tert-butylphenol (2.0 g) The same operation as in Example 1 was performed except that 1 H—perfluorobutanol (0.6 g, pK _a = 11) was used, and a polymer having the following structure (PC-8, T g: 183 ° C., [^ spc] = 1.23 d 1 Zg). The composition ratio of the polymer was confirmed by 'H-NMR (FIG. 8).

(PC-8) A photoconductor was prepared by the same method as that of Example 1 using (PC-8) as the binder resin and (C-2) as the charge transporting substance. At that time, no turbidity or gelation was observed in each coating solution even if left for one month. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _R ) after 5 seconds of light irradiation (10 Lux), half-exposure (E _1/2 ), and wear The amount of decrease in the charge transport layer due to was measured. The results are shown in Tables 3 and 4.

Example 2 1

Instead of 2,2-bis (4-hydroxyphenyl) propane (74 g) used in Example 1, 1,1-bis (4-hydroxyphenyl) cyclohexane (87 g), 2,2 3,3,4,4-Hexafluoro-1,5-pentanediol (15 g) instead of 1H, 1H, 6H, 6H-perfluoro; I, 6-Hexanediol (1 _{4 g, p K a = 1} 1), p- tert- Buchirufuwenoru the (2. O 1 H, 1 H- Pas one Furuorobu evening Knoll instead of g) (0. 6 g, p K a = 1 1) Except for using, the same operation as in Example 1 was carried out to obtain a copolymer having the following structure (PC-9, Tg: 154 ° C, [^ sp / c] = 0.78 d1 / g) I got The copolymer composition ratio was confirmed by ¹ H-NMR (FIG. 9).

 0

0— C-1 0— CH ₂ — (CF ₂ ) ₂ — CF ₃ ) _{0 01}

(PC-9) A photoconductor was prepared by the same method as that of Example 1 using (PC-9) as the binder resin and (C-12) as the charge transporting substance. At that time, leave each coating liquid for one month. However, no turbidity or gelation was observed. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _K ) after 5 seconds of light irradiation (1 OL ux), the half-life exposure (E _{l / 2} ), and the charge due to abrasion were obtained. The amount of decrease in the transport layer was measured. The results are shown in Tables 3 and 4. Example 22

Instead of 2,2-bis (4-hydroxyphenyl) propane (74 g) used in Example 1, 1,1-bis (4-hydroxyphenyl) cyclohexane (87 g), 2,2 Instead of 3,3,4,4-hexafluoro-1,5-pentendiol (15 g), 1 H, 1 H, 6H, 6H-perfluoro-1,6-hexanediol (13 g , PK _a = 1 1) and 2,2,2-tris (4-hydroxyphenyl) ethane (0.3 g), p-tert-butylphenol (2.0 g) instead of 1H, 1H —Perfluorobutanol (0.6 g, pK _a = 11, the same operation was performed as in Example 1 except for using a copolymer having the following structure (PC-10, T g: 1 57 ° C, was confirmed by [? sp / c] = 0. 87 d 1 / g) was obtained. copolymerization composition ratio ¹ H- NMR (Fig. 1 0).

(PC-10) A photoconductor was prepared in the same manner as in Example 1, except that (PC-10) was used as the binder resin and (C-2) was used as the charge transport material. At this time, no turbidity or gelation was observed even after leaving each coating solution for one month. In the same manner as in Example 1, the initial surface potential (V.) and the residual potential (V, j, halved after 5 seconds from light irradiation (1 OL ux)) The amount of exposure (E _1/2 ) and the amount of charge transport layer decrease due to abrasion were measured. The results are shown in Tables 3 and 4. Example 23

Instead of 2,2,3,3,4,4-hexafluoro-1,5-pentanediol (15 g) used in Example 1, 1H, 1H, 6H, 6H-perfluoro-1, The same operation as in Example 1 was performed except that 6-hexanediol (4.3 g, pK _a = 11) and bis (4-hydroxyphenyl) diphenylmethane (17 g) were used. A copolymer having the structure (PC-11, Tg: 152 ° C, / C]-0.55 d1 Zg) was obtained. The copolymer composition was confirmed by 'H-NMR (Fig. 11).

パインダ一樹脂として （PC— 1 1 ) 、 電荷輸送物質として （C一 2 ) を い、 実施例 1と同様の方法で感光体を作製した。 その際、 各塗工液は、 1か月. 置しても、 白濁、 ゲル化の発生は見られなかった。 また、 実施例 1と同様の方法 で初期表面電位 （V。） 、 光照射 （1 O L u x) 5秒後の残留電位 （V_K) 、 半減 露光量 （E, ₂) 及び摩耗による電荷輸送層の減少量を測定した。 結果を表 3及ひ 表 4に示す。 実施例 24

A photoconductor was prepared in the same manner as in Example 1, except that (PC-11) was used as the binder resin and (C-12) was used as the charge transport material. At that time, no turbidity or gelation was observed even when each coating solution was left for one month. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _K ) after 5 seconds of light irradiation (1 OL ux), the half-exposure exposure (E, ₂ ), and the charge transport layer due to abrasion were obtained. Was measured. The results are shown in Tables 3 and 4. Example 24

Binder resin used in Example 1 (Same as Example 1 except that 11 parts by weight of PC-11 was changed to 0.5 parts by weight of binder resin (PC-2) and 0.5 parts by weight of resin of Comparative Example 1. Each coating solution was left for one month. No turbidity or gelation was observed. In the same manner as in Example 1, the initial surface potential (V.), the residual potential (V _R ) after 5 seconds of light irradiation (1 OL ux), the half-exposure dose (E _1/2 ), and the charge transport due to abrasion. The amount of layer loss was measured. The results are shown in Tables 3 and 4. Example 2 5

Instead of 2,2-bis (4-hydroxyphenyl) propane (74 g) used in Example 1, 2,2,3,3,4,4-hexafluoro-1,5-pentanediol (69 g, Except for using pK _a = 1 1), the same operation as in Example 1 was performed, and a polymer having the following structure (PC — 12, [τ? _SP / c] = 0.6 2 d 1 / g) was obtained. The resulting ¹ H- NMR spectra The analysis of the polymer _{'H- NMR (CD 2 C 1} 2) δ = 4. 7 4 (4 Η, t, J = 1 3. 5 H z) It was p pm.

0

 II

+ 0— CH _2- (CF ₂ ) ₃ -CH ₂ -0-C-

0.05

(PC-1 2) A photoconductor was prepared in the same manner as in Example 1, using (pc-12) as the binder resin and (C-2) as the charge transporting substance. No turbidity or gelation was observed even after leaving for 1 month, and the initial surface potential (V.) and light irradiation (1 OL ux) for 5 seconds in the same manner as in Example 1. The residual potential (V _K ), the half-exposure exposure (E, ₂ ), and the decrease of the charge transport layer due to abrasion were measured, and the results are shown in Tables 3 and 4. Table 3 Initial surface potential V. (V) Retention potential V _R (V) Half-exposure dose E _1/2 (lux · sec)

 One 2 0.75

 One 5 0.72

 One 4 0.73

 One 3 0.75

 One 4 0.72

 One 6 0.74

一 2 0.73

One 2 0.73

Table 4

Comparative Example 5

Instead of 2,2,3,3,4,4-hexafluoro-1,5-pentanediol (15 g) used in Example 1, 1,5-pentanediol (15 g, pK _a = 1 7) The same operation as in Example 1 was performed except for using, and an attempt was made to synthesize a polymer. However, no polymer was obtained. Industrial applicability

The polymer of the present invention has good compatibility with a charge transport material, does not cause whitening or gelation even when dissolved in a solvent, and has excellent force, strength, and mechanical properties. An electrophotographic photoreceptor having high surface hardness and abrasion resistance when used as a binder resin for a photosensitive layer for photosensitivity can be provided. The above polymer and charge transport material Is dissolved in a solvent, the coating liquid of the present invention does not cause whitening or gelling over a long storage period, exhibits excellent stability, and does not cause crystallization of the binder resin during coating. By using the electrophotographic photosensitive member for forming the photosensitive layer, an electrophotographic photosensitive member exhibiting excellent electrophotographic characteristics over a long period of time can be obtained. Since the electrophotographic photoreceptor of the present invention uses the above polymer as a binder resin for the photosensitive layer, it maintains excellent abrasion resistance and electrophotographic properties over a long period of time, and has good cleanability. It also has aging characteristics.

Claims

1. Reduced viscosity at 20 ° C of a 0.5 g / d1 solution containing a repeating unit (1) represented by the following general formula (1) as a main component and methylene chloride as a solvent [20] _SP Z c] is 0.2 to 10.0 d 1. One 0— Rf ¹ — 0— C one (1)  II  0 contract (In the formula, R f ¹ is composed of at least a carbon atom and a fluorine atom, and is directly bonded to each oxygen atom of the carbonate bond in the general formula (1) without passing through an arylene group. Represents a group. 2. The polymer according to claim 1, wherein R f ′ is a group having a structure selected from the following group. ■ CH ₂ — (CF ₂ ) _r — CH ₂ —, -CH- — CH— CH ₂ — One CH— CH _2- I, I (CF ₂ ) _r F (CF ₂ ) _r F CH ₂ (CF ₂ ) _r F (CF ₂ ) _r F (CF ₂ ) _r F CH ₂ (CF ₂ ) _r F (CF ₂ ) _r F  I -C- One CH- CH- One CH— CH-, One C— CH _2- I (CF ₂ ) _S F (CF ₂ ) _S F CH ₂ (CF ₂ ) _S F (CF ₂ ) _S F one

(In the formula, r, s, u and v each independently represent an integer of 1 to 20.) 3. The main component is the repeating unit (1) represented by the general formula (1), and some or all of the polymer terminals are terminated by a terminal group (3) represented by the following general formula (3) The polymer according to claim 1. -OC-0-Rf ² (3)  II  0 (In the general formula (3), R f ² is composed of at least a carbon atom and a fluorine atom, and is directly bonded to an oxygen atom of the carbonate bond in the general formula (3) without passing through an arylene group. Represents a group.) 4. Polymer according to claim 3, wherein R ί ² is a group having a structure selected from the following group. F- (CF ₂ ) r ~ CH _2- , F— (CF ₂ ) _r — CHFCF ₂ CH _2- , F— (CF ₂ ) _r- (CH ₂ ) _s- , F- (CF ₂ ) _r O-CF-CH _2- , F- (CF ₂ ) _r -CF-CH _2- , H— (CF ₂ ) _r — CH ₂ —, CF ₃ CF ₃ F- (CF ₂ ) _S H- (CH ₂ ) _S H- (CH ₂ ) _s 0 F- (CF ₂ ) _r -CH-, F- (CF ₂ ) _r -CH-, F— (CF ₂ ) _r — CH- (In the formula, r and s each independently represent an integer of 1 to 20.) 5. Having a branch unit represented by the following general formula (4) as a repeating unit (4), and the ratio of the repeating unit (4) to the total of the repeating unit (4) and the repeating unit other than the repeating unit (4) The polymer according to claim 1 or 3, wherein is 0.1 to 30 mol%. _R 54  (Four)

(In the general formula (4), R ⁵⁴ represents an alkyl group having 1 to 10 carbon atoms.) 6. The repeating unit (1) represented by the following general formula (1) and the repeating unit (2) represented by the following general formula (2) are the main components, and the repeating unit (1) and the repeating unit (2) The ratio of the repeating unit (1) with respect to the total of the above is 0.1 to 99 mol%, and the reduced viscosity at 20 ° C of a 0.5 g / d 1 solution using methylene chloride as a solvent [ _SP / c] Is 0.2 to 10.0 d 1 / g. One 0— Rf ¹ — 0— C one (1)  II  0 (In the formula, R f ′ represents a group composed of at least a carbon atom and a fluorine atom and directly bonded to each oxygen atom of the carbonate bond in the general formula (1) without passing through an arylene group.)

(In the general formula (2), R ⁵ ° and R ^{5 are} each independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, substitution of 6 to 12 carbon atoms or It represents unsubstituted Ariru group, W is a single bond, - 0 -, one CO-, - S-, - SO_, - S0 2 -, - CR 52 R 53 - (R 52 and R ⁵³ are each independently, A hydrogen atom, a trifluoromethyl group, an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.), A cycloalkylidene group having 5 to 11 carbon atoms or carbon number 2 to 12 α, ω-alkylene group, 9-fluorenylidene group, 1,9-menthenyl group, substituted or unsubstituted pyradylidene group, substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or represents an α, ω-siloxanediyl group, and Α and Β each independently represent an integer of 0 to 4.) 7. The polymer according to claim 6, wherein R f ¹ is a group having a structure selected from the following group. -CH _2- (CF ₂ ) r-CH2-, -CH- One CH— CH _2- , One CH— CH ₂ — (CF ₂ ) _r F (CF ₂ ) _r F CH ₂ (CF ₂ ) _r F (CF ₂ ) _r F (CF ₂ ) _r F CH ₂ (CF ₂ ) _r F (CF ₂ ) _r F -C- -CH-CH--CH- CH—, one C-one CH _2- (CF ₂ ) _S F (CF ₂ ) _S F CH ₂ (CF ₂ ) _S F (CF ₂ ) _S F) _r F

(CF ₂ ) vF (CF ₂ ) _S F (In the formula, r, s, u and v each independently represent an integer of 1 to 20.) 8. The repeating unit (1) represented by the general formula (1) and the repeating unit (2) represented by the general formula (2) are the main components, and a part or all of the polymer terminal is represented by the following general formula (3) 7. The polymer according to claim 6, wherein the polymer is terminated with a terminal group (3) represented by:

(In the general formula (3), R f ² represents a group composed of at least a carbon atom and a fluorine atom and directly bonded to an oxygen atom of a carbonate bond in the general formula (3) without passing through an arylene group. ) 9. The polymer according to claim 8, wherein R f ² is a group having a structure selected from the following group. F- (CF ₂ ) _r -CH _2- , F- (CF ₂ ) r-CHFCF ₂ CH2-, F-(CF ₂ ) _r — (CH ₂ ) _S — F— (CF ₂ ) _r 0— CF—CH ₂ —, F- (CF ₂ ) _r -CF-CH ₂ —, H— (CF ₂ ) _r — CH ₂ -CF ₃ CF ₃ F- (CF ₂ ) _S H- (CH ₂ ) _S H- (CH ₂ ) _s 0 F— (CF ₂ ) _r — CH—, F- (CF ₂ ) _r -CH-, F- (CF ₂ ) _r -CH- (In the formula, r and s each independently represent an integer of 1 to 20.) 10. The repeating unit (4) has a branch unit represented by the following general formula (4) as a repeating unit (4), and represents a repeating unit (4) based on the sum of the repeating unit (4) and the repeating unit other than the repeating unit (4). 9. The polymer according to claim 6, wherein the proportion of the polymer is 0.01 to 30 mol%. _R 54

(In the general formula (4), R ⁵⁴ represents an alkyl group having 1 to 10 carbon atoms.) 1 1. The main component is a repeating unit (2) represented by the following general formula (2), and a part or all of the terminal of the polymer is terminated by a terminal group (3) represented by the following general formula (3). The reduced viscosity [?? _sP Zc] at 20 ° C of a solution with a concentration of 0.5 g / d1 in methylene chloride as a solvent should be 0.2 ~: 10.0 d1 Zg. A polymer characterized by the following. (2)

(In the general formula (2), R ⁵ and R ⁵ ′ are each independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, or a substitution having 6 to 12 carbon atoms. or represents unsubstituted Ariru group, W is a single bond, one 0-, -CO-, one S -, one SO - one _{^{S0 2 -, _CR 52 R 53}} - (R 52 and R ⁵³ are each independently A hydrogen atom, a trifluoromethyl group, an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.), A cycloalkylidene group having 5 to 11 carbon atoms or carbon number 2- to 12-, ω-alkylene group, 9-fluorenylidene group, 1,9-methylbenzyl group, substituted or unsubstituted pyradylidene group, substituted or unsubstituted arylene having 6 to 12 carbon atoms Represents a group or an α, ω-siloxanediyl group, and Α and Β each independently represent an integer of 0 to 4.) -OC-0-Rf ² (3)  II  0 (In the general formula (3), R f ² is a group composed of at least a carbon atom and a fluorine atom and directly bonded to an oxygen atom of a carbonate bond in the general formula (3) without passing through an arylene group. Represents.) 12. The polymer according to claim 11, wherein R f ² is a group having a structure selected from the following group. F- (CF ₂ ) _r -CH _2- , F- (CF ₂ ) _r — CHFCF ₂ CH ₂ —, F— (CF ₂ ) _r — (CH ₂ ) _S- , F- (CF ₂ ) _r 0-CF-CH _2- , F— (CF ₂ ) _r — CF— CH ₂ —, H— (CF ₂ ) _r — CH ₂ —, CF ₃ CF ₃ F- (CF ₂ ) _S H- (CH ₂ ) _S H- (CH ₂ ) _s 0 F- (CF ₂ ) _r -CH-, F- (CF ₂ ) _r -CH-, F— (CF ₂ ) _r — CH- (In the formula, r and s each independently represent an integer of 1 to 20.) 1 3. A branch unit represented by the following general formula (4) is used as a repeating unit (4). The weight according to claim 11, wherein the ratio of the repeating unit (4) to the total of the repeating unit (4) and the repeating unit other than the repeating unit (4) is 0.01 to 30 mol%. Coalescing. One 0 — 〈/ c— <fVo-c- (4)  0 0—C-one  II 0 (In the general formula (4), R ⁵⁴ represents an alkyl group having 1 to 10 carbon atoms.) 1 4. A resin coating liquid comprising the polymer according to claim 1, a charge transport substance, and a solvent. 1 5. A resin coating liquid comprising the polymer according to claim 6, a charge transport substance, and a solvent. 1 6. A resin coating liquid comprising the polymer according to claim 11, a charge transport substance, and a solvent. 1 7. An electrophotographic photoreceptor having a photosensitive layer containing a charge generating substance, a charge transporting substance and a binder resin on a conductive substrate, wherein the photosensitive layer uses the polymer according to claim 1 as a binder resin. An electrophotographic photosensitive member characterized by the following. 1 8. An electrophotographic photosensitive member having a photosensitive layer containing a charge generating substance, a charge transporting substance and a binder resin on a conductive substrate, wherein the photosensitive layer uses the polymer according to claim 6 as a binder resin! ^ An electrophotographic photoreceptor characterized by the fact that: 1 9. Contain charge generation material, charge transport material and binder resin on conductive substrate An electrophotographic photosensitive member having a photosensitive layer, wherein the photosensitive layer uses the polymer according to claim 11 as a binder resin. 20. In a method for producing polycarbonate, an interfacial polycondensation is carried out in a mixed solution of an organic solvent insoluble in water and an aqueous alkali solution using a carbonate-forming compound and a dioxy compound in the presence of an aqueous solution of alkali metal. A method for producing a polycarbonate, comprising using a dihydric alcohol having _a pk _{a in} water at 25 ° C of less than 15.74 as a dioxy compound. 2 1. with pk _a is 1 5. small again dihydric alcohols than 74 in water at 2 5 ° C as Jiokishi compound, as a chain terminator 2 5 ° pk _a of the underwater C 1 5.7 4 20. The production method according to claim 20, wherein a smaller monohydric alcohol is used. 22. The process according to claim 20, wherein as the dioxy compound, _a dihydric alcohol having a pKa in water at 25 ° C of less than 15.74 and a dihydroxyaryl compound represented by the following general formula (II) are used. Method.

(Wherein, R ⁵ and R ⁵¹ are each independently a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, a substituted or unsubstituted aryl having 6 to 12 carbon atoms) W represents a single bond, one 0—, —CO—, one S—, —SO—, —SO, one, one CR ⁵² R ⁵³ — (R ⁵² and R ⁵³ each independently represent a hydrogen atom, A trifluoromethyl group, an alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.), A cycloalkylidene group having 5 to 11 carbon atoms or 2 to 12 carbon atoms Α, ω-alkylene group, 9-fluorenylidene group, 1,9-menthenyl group, substituted or unsubstituted pyradylidene group, substituted or unsubstituted carbon number of 6 to 12 represents an arylene group or α, ω-siloxanediyl group, and Α and Β each independently represent an integer of 0 to 4. ) 23. A dihydric alcohol having a pk _a in water at 25 ° C of less than 15.74 and a dihydroxylaryl compound represented by the above general formula (II) as a dioxy compound, and a terminal stopper at 25 ° C the process according to the range 22 of claims using small again monohydric alcohol from pk _a is 15.74 in water at. 24. A method for producing a polycarbonate, which comprises subjecting a carbonate-forming compound and a dioxy compound to interfacial polycondensation in a mixed solution of an organic solvent insoluble in water and an aqueous alkaline solution in the presence of an aqueous solution of an aqueous solution, A polyhydroxylaryl compound represented by the following general formula (II) as a dioxy compound, and _a monohydric alcohol having _a pka of less than 15.74 in water at 25 ° C as a terminal terminator is used. Bonnet manufacturing method.

(Wherein, R ⁵ and R ⁵ ′ each independently represent a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. represents an aryl group, W is a single bond, - 0-, one CO -, - S-, - SO-, - S0 ₂ ^{one, - CR 52 R 5 3 -} (R 52 and R ⁵³ each independently, hydrogen Atom, trifluoromethyl group, alkyl group having 1 to 10 carbon atoms or substituted or unsubstituted aryl group having 6 to 12 carbon atoms.), Cycloalkylidene group having 5 to 11 carbon atoms or 2 carbon atoms , 12-, ω-alkylene group, 9-fluorenylidene group, 1,9-nonyl benzyl group, substituted or unsubstituted pyradylidene group, substituted or unsubstituted arylene group having 6 to 12 carbon atoms Or represents an α, ω-siloxanediyl group, and Α and Β each independently represent an integer of 0 to 4.)